79560-19-3

Basic information

• Product Name: 4-(3,4-Dichlorophenyl)-1-tetralone
• Synonyms: 4-(3,4-DICHLOROPHENYL)-3,4-DIHYDRONAPHTHALEN-1-(2H)-ONE;4-(3',4'-DICHLOROPHENYL)-1-TETRALONE;4-(3,4-DICHLOROPHENYL)-1-TETRALONE;4-(3,4-DICHLOROPHENYL)-3,4-DIHYDRO-1(2H)-NAPHTALENE-1-ONE;4-(3,4-DICHLOROPHENYL)-3,4-DIHYDRO-1(2H)-NAPHTHALENE-1-ONE;4-(3,4-DICHLOROPHENYL)-3,4-DIHYDRO-1(2H)-NAPHTHALENONE;4-(3,4-DICHLOROPHENYL)-3,4-DIHYDRO-1(2H)-NAPHTHALENE-1-ONE (SERTRALONE);4-(3,4-Dichlorophenyl)-3,4-dihydronaphthalene-1(2H)-one
• CAS NO: 79560-19-3
• Molecular Formula: C₁₆H₁₂Cl₂O
• Molecular Weight: 291.17
• Product Categories: Miscellaneous;INTERMEDIATESOFSERTRALINE;API intermediates;(intermediate of sertraline);Setraline;Miscellaneous Reagents;Aromatics;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 79560-19-3.mol
• Article Data: 29

Chemical Properties

• Melting Point: 97-99°C
• Boiling Point: 403 °C at 760 mmHg
• Flash Point: 170.3 °C
• Appearance: off-white crystalline solid
• Density: 1.318 g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)
• CAS DataBase Reference: 4-(3,4-Dichlorophenyl)-1-tetralone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3,4-Dichlorophenyl)-1-tetralone(79560-19-3)
• EPA Substance Registry System: 4-(3,4-Dichlorophenyl)-1-tetralone(79560-19-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 79560-19-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Crystalline Solid

Synthetic route

4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol (866018-46-4) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
With oxygen; sodium hydride In tetrahydrofuran at 0 - 20℃; for 5h;	98%
With acetone In toluene at 80℃; for 0.333333h; Flow reactor;	95%
With pyridinium chlorochromate In dichloromethane at 20℃; for 8h; Inert atmosphere;	80%

rac-5-(3,4-dichlorophenyl)dihydrofuran-2(3H)-one (95609-48-6) + benzene (71-43-2) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
With hydrogen fluoride for 18h; Ambient temperature;	97%

4-(3,4-dichlorophenyl)-4-phenylbutanoic acid (79560-18-2) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
With boron trifluoride diethyl etherate; trifluoroacetic anhydride In dichloromethane at 40 - 45℃; for 5h; Product distribution / selectivity;	93%
With chlorosulfonic acid In dichloromethane at 20℃; for 1h;	87%
With Eaton’s reagent at 20℃; Inert atmosphere;	83%
Stage #1: 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid With sulfuric acid In benzene at 23 - 80℃; for 8h; Stage #2: With sodium hydroxide In water Product distribution / selectivity;	65%
Multi-step reaction with 2 steps 1: SOCl2 / toluene / 1.25 h 2: AlCl3 / CS2 / 16 h / Ambient temperature View Scheme

α-naphthol (90-15-3) + 1,2-dichloro-benzene (95-50-1) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
With aluminum (III) chloride at 100℃; for 1.5h; Inert atmosphere;	82%
Stage #1: α-naphthol; 1,2-dichloro-benzene With aluminum (III) chloride at 65℃; for 5h; Stage #2: With water In ethyl acetate for 0.5h;	82%
With aluminium trichloride at 100℃; for 1h;	80%

4-(3,4-dichlorophenyl)tetrahydronaphthalone tosylhydrazone → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 3.5h; Oxidation; oxidative cleavage;	80%

α-naphthol (90-15-3) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
With aluminum tri-bromide In methanol; water; 1,2-dichloro-benzene	79.6%

(E)-N-(4-nitrophenyl)-4-phenylbut-3-enamide + 1,2-dichloro-benzene (95-50-1) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
With trifluorormethanesulfonic acid at 50℃; for 16h; Friedel Crafts acylation; Inert atmosphere;	76%

di-isopropylic ether + α-naphthol (90-15-3) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
aluminium chloride In water; 1,2-dichloro-benzene	50.9%

4-bromomethylene-1-(3,4-dichlorophenyl)-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydronaphthalene → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
Stage #1: 4-bromomethylene-1-(3,4-dichlorophenyl)-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydronaphthalene With osmium(VIII) oxide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium periodate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; water at 25℃; for 1h; Inert atmosphere;	47%

α-naphthol (90-15-3) + 1,2-dichloro-benzene (95-50-1) → 4-(2,3-dichlorophenyl)-3,4-dihydro-1(2H)-naphthone + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
With aluminum (III) chloride at 100℃; for 4h; Inert atmosphere;	A n/a B 45%
With aluminum (III) chloride at 100℃; for 4h;	A n/a B 45%
Stage #1: α-naphthol; 1,2-dichloro-benzene With aluminum (III) chloride at 98℃; for 1.5h; Stage #2: With water In ethyl acetate for 0.5h;	A 6.2 g B n/a

4-(3,4-dichlorophenyl)-4-phenylbutyric acid (149620-65-5) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
With aluminium trichloride In carbon disulfide for 16h; Ambient temperature; Yield given;

3,4-dichlorobenzophenone (6284-79-3) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium tert-butoxide / 2-methyl-propan-2-ol / 16 h / Heating 2: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating 3: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 4: SOCl2 / toluene / 1.25 h 5: AlCl3 / CS2 / 16 h / Ambient temperature View Scheme

4-(3,4-dichlorophenyl)-4-phenylbut-3-enoic acid (79560-17-1) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 2: SOCl2 / toluene / 1.25 h 3: AlCl3 / CS2 / 16 h / Ambient temperature View Scheme

3-(ethoxycarbonyl)-4-(3,4-dichlorophenyl)-4-phenylbut-3-enoic acid (79560-16-0) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating 2: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 3: SOCl2 / toluene / 1.25 h 4: AlCl3 / CS2 / 16 h / Ambient temperature View Scheme

3-(3,4-dichlorobenzoyl)-propionic acid (50597-19-8) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaOH (pH 10.73), NaBH4 / 2 h / 78 °C 2: aq. HCl / 1) 65 - 70 deg C, 4 h, 2) rt, 16 h 3: 97 percent / anh. hydrogen fluoride / 18 h / Ambient temperature View Scheme

4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid (118528-87-3) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HCl / 1) 65 - 70 deg C, 4 h, 2) rt, 16 h 2: 97 percent / anh. hydrogen fluoride / 18 h / Ambient temperature View Scheme

1,2-dichloro-benzene (95-50-1) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / AlCl3 / 2.5 h / 60 °C 2: aq. NaOH (pH 10.73), NaBH4 / 2 h / 78 °C 3: aq. HCl / 1) 65 - 70 deg C, 4 h, 2) rt, 16 h 4: 97 percent / anh. hydrogen fluoride / 18 h / Ambient temperature View Scheme

N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine (79560-20-6) → cis-(1S,4S)-N-methyl-(3-chlorophenyl)-1,2,3,4-tetrahydro-1-naphtalenamine (871838-58-3) + (1S)-cis-N-methyl-4-(4-chlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (91797-63-6) + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) + trans-(1S,4R)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (91797-60-3) + Sertraline (79617-96-2)

Conditions	Yield
With hydrogen; SA-3135 support, Co(NO3)2, H2O; dried and calcined ones or twice (Co 11 - 25percent); reduction with H2 In tetrahydrofuran at 120 - 150℃; under 6000.6 Torr;	A n/a B n/a C 0.2 - 0.7 %Chromat. D 7 - 9.4 %Chromat. E 87 - 91 %Chromat.

rac-5-(3,4-dichlorophenyl)dihydrofuran-2(3H)-one (95609-48-6) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
With sodium hydroxide; trifluorormethanesulfonic acid In hexane; dichloromethane; benzene
With sodium hydroxide; trifluorormethanesulfonic acid In hexane; dichloromethane; benzene

hydrofluoric acid (hydrogen fluoride) + rac-5-(3,4-dichlorophenyl)dihydrofuran-2(3H)-one (95609-48-6) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
With sodium hydroxide In hexane; dichloromethane; water; polypropylene; benzene
With sodium hydroxide In hexane; dichloromethane; water; polypropylene; benzene

C24H21BrCl2O3S → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 5 h / 25 °C / Inert atmosphere 2.1: osmium(VIII) oxide / tetrahydrofuran; water; 1-methyl-pyrrolidin-2-one / 2 h / 25 °C / Inert atmosphere 2.2: 1 h / 25 °C / Inert atmosphere View Scheme

isopropenylbenzene (98-83-9) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid; N-Bromosuccinimide / dichloromethane / Reflux 2.1: potassium carbonate / acetone / 0.17 h / 25 °C / Inert atmosphere 2.2: 10 h / Inert atmosphere 3.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 0 °C / Inert atmosphere 4.1: boron trifluoride diethyl etherate / dichloromethane / 5 h / 25 °C / Inert atmosphere 5.1: osmium(VIII) oxide / tetrahydrofuran; water; 1-methyl-pyrrolidin-2-one / 2 h / 25 °C / Inert atmosphere 5.2: 1 h / 25 °C / Inert atmosphere View Scheme

5-bromo-1-(3,4-dichlorophenyl)-4-phenyl-2-(toluene-4-sulfonyl)pent-4-en-1-one → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 0 °C / Inert atmosphere 2.1: boron trifluoride diethyl etherate / dichloromethane / 5 h / 25 °C / Inert atmosphere 3.1: osmium(VIII) oxide / tetrahydrofuran; water; 1-methyl-pyrrolidin-2-one / 2 h / 25 °C / Inert atmosphere 3.2: 1 h / 25 °C / Inert atmosphere View Scheme

(3,4-dichlorophenyl)-2-[(4-methylphenyl)sulfonyl]-1-ethanone → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 0.17 h / 25 °C / Inert atmosphere 1.2: 10 h / Inert atmosphere 2.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 0 °C / Inert atmosphere 3.1: boron trifluoride diethyl etherate / dichloromethane / 5 h / 25 °C / Inert atmosphere 4.1: osmium(VIII) oxide / tetrahydrofuran; water; 1-methyl-pyrrolidin-2-one / 2 h / 25 °C / Inert atmosphere 4.2: 1 h / 25 °C / Inert atmosphere View Scheme

1,3-dibromo-2-phenylprop-1-ene (112635-43-5, 112635-44-6) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 0.17 h / 25 °C / Inert atmosphere 1.2: 10 h / Inert atmosphere 2.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 0 °C / Inert atmosphere 3.1: boron trifluoride diethyl etherate / dichloromethane / 5 h / 25 °C / Inert atmosphere 4.1: osmium(VIII) oxide / tetrahydrofuran; water; 1-methyl-pyrrolidin-2-one / 2 h / 25 °C / Inert atmosphere 4.2: 1 h / 25 °C / Inert atmosphere View Scheme

2-<(2,2-dimethylpropanoyl)oxy>-1-phenylethanone (2522-81-8) → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: magnesium / tetrahydrofuran / 20 °C / Inert atmosphere 1.2: -45 °C / Inert atmosphere 2.1: Eaton’s reagent / dichloromethane / 20 °C / Inert atmosphere 3.1: sodium methylate / diethyl ether / 0 - 20 °C 4.1: dichloromethane / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C 6.1: potassium hydroxide; water / ethanol / 20 °C 7.1: Eaton’s reagent / 20 °C / Inert atmosphere View Scheme

2-(3,4-dichlorophenyl)-2-hydroxy-2-phenylethyl Pivalate → 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: Eaton’s reagent / dichloromethane / 20 °C / Inert atmosphere 2: sodium methylate / diethyl ether / 0 - 20 °C 3: dichloromethane / Inert atmosphere 4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C 5: potassium hydroxide; water / ethanol / 20 °C 6: Eaton’s reagent / 20 °C / Inert atmosphere View Scheme

trifluoromethylsulfonic anhydride (358-23-6) + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → 4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1-yl trifluoromethanesulfonate

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 0 - 20℃; for 0.5h;	99%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → 4-(3,4-dichloro-phenyl)-3,4-dihydro-2H-naphthalen-1-one oxime (152642-35-8)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 4h; Reflux; Industrial scale;	97%
With Amberlist A-21; hydroxylamine hydrochloride In tetrahydrofuran at 20℃;

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → (E)-4-(3,4-dichlorophenyl)-2-((dimethylamino)methylene)-3,4-dihydronaphthalen-1(2H)-one (1234376-86-3)

Conditions	Yield
at 110℃; for 24h;	97%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 1-chloro-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalene-2-carbaldehyde (1290541-37-5)

Conditions	Yield
With trichlorophosphate at 0 - 65℃; for 4h; Vilsmeier-Haack Formylation;	97%
With trichlorophosphate at 0 - 65℃; for 4h; Vilsmeier-Haack reaction;	78%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) + methylamine (74-89-5) → (4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-ylidene)methylamine (261776-41-4)

Conditions	Yield
In water; ethylene glycol at 60℃; for 4h; Product distribution / selectivity;	96%
In 2-methoxy-ethanol; water at 25 - 45℃; for 5.5h; Product distribution / selectivity;	92%
With titanium tetrachloride In diethyl ether at -35 - 20℃; Condensation;	91%

3,4,5-trimethoxy-benzaldehyde (86-81-7) + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → 4-(3,4-dichlorophenyl)-2-(3,4,5-trimethoxy-benzylidene)-3,4-dihydro-naphthalen-1(2H)-one

Conditions	Yield
With ammonium acetate for 0.0166667h; Knoevenagel condensation; microwave irradiation;	96%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) + benzylamine (100-46-9) → N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidine]benzylamine

Conditions	Yield
In toluene for 7h; Heating / reflux;	96%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) + methylamine (74-89-5) → N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine (79560-20-6)

Conditions	Yield
In ethanol at 0℃; Solvent; Heating; Industrial scale; Large scale;	95%
With formic acid In methanol	95%
With thionyl chloride In tetrahydrofuran at -10 - 20℃;	93%

methylamine hydrochloride (593-51-1) + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → sertraline (140631-53-4)

Conditions	Yield
Stage #1: methylamine hydrochloride; 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one With potassium hydroxide In methanol at 25 - 30℃; for 24h; Stage #2: With sodium tetrahydroborate In methanol at -5 - 25℃; for 12 - 14h;	95%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) + (S)-2-methylpropane-2-sulfinamide (343338-28-3) → (S)-N-(4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-ylidene)-2-methylpropane-2-sulfinamide

Conditions	Yield
With titanium(IV) isopropylate In neat (no solvent) at 70℃; for 4h; Reagent/catalyst; Solvent;	95%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → ((4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1-yl)oxy)trimethylsilane

Conditions	Yield
With trialkylamine In dichloromethane at 0℃; for 0.5h;	95%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidine]-3,4-dimethoxy-benzylamine

Conditions	Yield
With 3,4-dimethoxybenzylamine	92.3%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) + Diethyl carbonate (105-58-8) → 4-(3,4-dichlorophenyl)-1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester (944054-46-0)

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil for 48h; Inert atmosphere;	90%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidine]-4-chlorobenzylamine

Conditions	Yield
With 4-chlorobenzylamine	89.4%

4-(2,3-dichlorophenyl)-3,4-dihydro-1(2H)-naphthone + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) + methylamine (74-89-5) → N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine (79560-20-6)

Conditions	Yield
methanesulfonic acid In ethanol at 0 - 70℃; for 4h;	88%
methanesulfonic acid In acetonitrile at 0 - 70℃; for 4h;	88%
In triethylamine at 0 - 90℃; for 10h;	87%
toluene-4-sulfonic acid In triethylamine at 0 - 50℃; for 4h;	82%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → N-[4-(3,4-dichlorophenyl)-3,4-dihydronaphthalenylidine]-4-methoxybenzylamine

Conditions	Yield
With 4-methoxy-benzylamine	85.6%

4-amino-6-chloroquinoline-3-carbaldehyde (1307301-10-5) + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → 2-chloro-9-(3,4-dichloro-phenyl)-8,9-dihydrobenzo[h]naphtho[1,2-b][1,6]naphthyridine (1338818-61-3)

Conditions	Yield
With piperidine; potassium hydroxide In N,N-dimethyl-formamide for 3h; Friedlaender synthesis; Reflux;	85%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) + benzaldehyde (100-52-7) → (2E)-(2-benzylidene)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-one (1177848-21-3)

Conditions	Yield
With potassium hydroxide In ethanol; water at 30℃;	85%
With potassium hydroxide In ethanol; water at 30℃; Claisen-Schmidt Condensation;	85%

2-amino-6-methoxyquinoline-3-carbaldehyde (477940-97-9) + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → 5-(3,4-dichlorophenyl)-10-methoxy-5,6-dihydrobenzo[b]naphtho[2,1-g][1,8]naphthyridine (1374543-22-2)

Conditions	Yield
With potassium hydroxide In ethanol for 3h; Friedlaender synthesis; Reflux;	85%
With potassium hydroxide In ethanol for 3h; Friedlaender Quinoline Synthesis; Reflux;	85%

N-methylhydroxyamine hydrochloride (4229-44-1) + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine N-oxide

Conditions	Yield
With sodium acetate In ethanol; water for 6h; Reflux; Industrial scale;	85%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) + 2-amino quinoline 3-carbaldehyde (75353-62-7) → 5-(3,4-dichlorophenyl)-5,6-dihydrobenzo[b]naphtho[2,1-g][1,8]naphthyridine (1374543-21-1)

Conditions	Yield
With potassium hydroxide In ethanol for 3h; Friedlaender synthesis; Reflux;	84%
With potassium hydroxide In ethanol for 3h; Friedlaender Quinoline Synthesis; Reflux;	84%

4-fluorobenzaldehyde (459-57-4) + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → C23H15Cl2FO (1227614-46-1)

Conditions	Yield
With potassium hydroxide In ethanol; water at 30℃;	83%
With potassium hydroxide In ethanol; water at 30℃; Claisen-Schmidt Condensation;	83%

4-amino-3-(4-chlorophenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (1294502-92-3) + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → 1-(4-chlorophenyl)-8-(3,4-dichlorophenyl)-3-phenyl-7,8-dihydro-3H-naphtho[1,2-b]pyrazolo-[3,4-h][1,6]naphthyridine (1359972-73-8)

Conditions	Yield
With potassium hydroxide In ethanol Friedlaender synthesis; Reflux;	83%

4-amino-3-(4-bromophenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (1294502-93-4) + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → 1-(4-bromophenyl)-8-(3,4-dichlorophenyl)-3-phenyl-7,8-dihydro-3H-naphtho[1,2-b]pyrazolo-[3,4-h][1,6]naphthyridine (1359972-74-9)

Conditions	Yield
With potassium hydroxide In ethanol Friedlaender synthesis; Reflux;	83%

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) + methylamine (74-89-5) → (+/-)-N-methyl-[(cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amine hydrochloride

Conditions	Yield
Stage #1: 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one; methylamine With thionyl chloride In tetrahydrofuran at -10 - 20℃; Stage #2: With potassium chloride; hydrogen; palladium on activated charcoal In tetrahydrofuran; methanol; water at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; methanol; water at 20℃;	82%

4-chlorobenzaldehyde (104-88-1) + 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (79560-19-3) → C23H15Cl3O (1227614-47-2)

Conditions	Yield
With potassium hydroxide In ethanol; water at 30℃;	81%
With potassium hydroxide In ethanol; water at 30℃; Claisen-Schmidt Condensation;	81%

Upstream product

• 95-50-1 1,2-dichloro-benzene 
• 312692-85-6 (3,4-dichlorophenyl)zinc(II) iodide 
• 100-42-5 styrene 
• 20555-91-3 3,4-dichloroiodobenzene 
• 108-86-1 bromobenzene 
• 2522-81-8 2-<(2,2-dimethylpropanoyl)oxy>-1-phenylethanone 
• 112635-43-5 1,3-dibromo-2-phenylprop-1-ene 
• 98-83-9 isopropenylbenzene 
• 866018-46-4 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol 
• 90-15-3 α-naphthol 
• 95609-48-6 rac-5-(3,4-dichlorophenyl)dihydrofuran-2(3H)-one 
• 79560-20-6 N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine 

Downstream Products

• 79617-95-1 cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine 
• 79836-45-6 trans-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine 
• 1271002-87-9 C₂₂H₂₅Cl₂NO₂ 
• 79559-97-0 sertraline hydrochloride 
• 155748-61-1 (4R)-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone 
• 124379-29-9 (4S)-4-(3,4-dichlorophenyl)-1-tetralone 
• 267884-85-5 cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine 
• 167026-37-1 (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ol 
• 1346228-87-2 (1S,4S)-1-(benzyloxy)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene 
• 1346228-88-3 benzyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate 
• 1346228-89-4 benzyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl(methyl)carbamate 
• 167026-40-6 (1R,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol 
• 1290541-37-5 1-chloro-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalene-2-carbaldehyde 
• 1359972-74-9 1-(4-bromophenyl)-8-(3,4-dichlorophenyl)-3-phenyl-7,8-dihydro-3H-naphtho[1,2-b]pyrazolo-[3,4-h][1,6]naphthyridine 

Relevant articles and documents

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Method for preparing serrine hydrochloride intermediate and impurities

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