52250-50-7

Basic information

• Product Name: 1-Phenyl-3,4-dihydroisoquinoline
• Synonyms: 1-PHENYL-3,4-DIHYDRO-ISOQUINOLINE;AKOS 213-253;1-phenyl-3,4-dihydroisochinoline;3,4-Dihydro-1-phenylisoquinoline;3,4-Dihydro-1-phenylisoquinoline HCl;Phenyl-3,4-dihydroisoquinoline;Solifenacin Related Compound 6
• CAS NO: 52250-50-7
• Molecular Formula: C₁₅H₁₃N
• Molecular Weight: 207.27
• Product Categories: Dihydroisoquinolines
• Mol File: 52250-50-7.mol
• Article Data: 55

Chemical Properties

• Melting Point: 174 °C
• Boiling Point: 326.5 °C at 760 mmHg
• Flash Point: 143.4 °C
• Appearance: /
• Density: 1.07 g/cm³
• Vapor Pressure: 0.000408mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 5.29±0.20(Predicted)
• CAS DataBase Reference: 1-Phenyl-3,4-dihydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenyl-3,4-dihydroisoquinoline(52250-50-7)
• EPA Substance Registry System: 1-Phenyl-3,4-dihydroisoquinoline(52250-50-7)

Safety Data

• Hazardous Substances Data: 52250-50-7(Hazardous Substances Data)

Usage

Description

1-Phenyl-3,4-dihydroisoquinoline is an organic compound belonging to the isoquinoline family. It is characterized by its unique molecular structure, which features a phenyl group attached to a dihydroisoquinoline ring. 1-Phenyl-3,4-dihydroisoquinoline is known for its potential applications in various fields due to its chemical properties.

Uses

1. Used in Pharmaceutical Industry:
1-Phenyl-3,4-dihydroisoquinoline is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
2. Used in Chemical Synthesis:
1-Phenyl-3,4-dihydroisoquinoline serves as a valuable building block in the preparation of a wide range of organic compounds, including 1,2,3,4-Tetrahydro-2-methyl-1-phenyl-1-isoquinolinecarbonitrile derivatives. These derivatives can be further utilized in the development of new chemical products with diverse applications.
3. Used in Research and Development:
1-Phenyl-3,4-dihydroisoquinoline is also employed in research and development laboratories for studying its chemical properties and potential applications. Its unique structure makes it an interesting subject for scientific investigation, which could lead to the discovery of new compounds and applications.

InChI:InChI=1/C15H13N/c1-2-7-13(8-3-1)15-14-9-5-4-6-12(14)10-11-16-15/h1-9H,10-11H2

Synthetic route

N-(2-phenethyl)benzimidoyl chloride (60943-13-7) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
With tin(IV) chloride In chloroform for 100h;	97%

N-phenethylbenzamide (3278-14-6) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
With 2-chloropyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 45℃; Bischler-Napieralski reaction; Inert atmosphere;	95%
With polyphosphoric acid at 180 - 200℃;	95%
With phosphorus pentoxide; trichlorophosphate In 5,5-dimethyl-1,3-cyclohexadiene Bischler-Napieralski Reaction; Reflux;	92%

1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
With N,N-dimethyl-formamide at 100℃;	94%
With potassium phosphate tribasic trihydrate; 5%-palladium/activated carbon; oxygen In acetonitrile at 60℃; Reagent/catalyst; Solvent; Green chemistry; chemoselective reaction;	86%
With sulfur In pyridine 1.) 3 h, 100 deg C, 2.) 12 h, r.t.;	40%

1-phenyl-2-tosyl-1,2,3,4-tetrahydroisoquinoline → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
With sodium hydroxide In water; dimethyl sulfoxide at 70℃; for 1.5h; regiospecific reaction;	91%

1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8, 96719-89-0, 118864-75-8)

Conditions	Yield
With hydrogenchloride; borane-ammonia complex In aq. phosphate buffer at 37℃; pH=7.8;	A n/a B 90%

N-oxy phenyl-1 dihydro-3,4-isoquinoleine (86448-84-2) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
With sodium hydroxide; sodium hydrogen telluride In ethanol for 18h; Heating; at pH 10-11;	88%

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (180272-45-1) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
With dimethyl sulfoxide at 100℃; for 24h; Solvent; Temperature; Schlenk technique; Green chemistry; chemoselective reaction;	87%
Multi-step reaction with 2 steps 1: trichloroisocyanuric acid / dichloromethane / 1.5 h / 3 - 5 °C 2: potassium hydroxide / methanol / 1 h / 20 °C View Scheme
With hydrogenchloride; oxygen In aq. phosphate buffer at 37℃; pH=7.8;
With air In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique; Green chemistry;

1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8) → 1-phenylisoquinoline (3297-72-1) + 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
With potassium phosphate tribasic trihydrate; palladium on activated charcoal; oxygen In acetonitrile at 60℃; for 17h; Solvent; Temperature; Reagent/catalyst;	A n/a B 86%
With air In N,N-dimethyl-formamide at 100℃; for 24h; Temperature; Solvent; Concentration; Schlenk technique; Green chemistry;	A n/a B 83%
With sodium carbonate In ethyl acetate at 120℃; for 24h; Sealed tube; Green chemistry; Overall yield = 99 %;	A 22% B 77%

1-phenyl-2-tosyl-1,2,3,4-tetrahydroisoquinoline → 1-phenylisoquinoline (3297-72-1) + 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
With sodium hydroxide In water; dimethyl sulfoxide at 125℃; for 2h; Inert atmosphere;	A 9% B 83%

1-(methylsulfanyl)-3,4-dihydroisoquinoline (14157-05-2) + phenylboronic acid (98-80-6) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate In tetrahydrofuran for 0.75h; Inert atmosphere; Reflux;	78%

2-phenylethanol (60-12-8) + benzonitrile (100-47-0) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
With 2-fluoropyridine; trifluoromethylsulfonic anhydride In 1,2-dichloro-ethane at 0 - 80℃; for 12.5h;	75%

N-phenethylbenzamide (3278-14-6) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + N-Benzoyl-N.N'-diphenaethyl-benzamidin (103162-83-0)

Conditions	Yield
With trichlorophosphate In 1,2-dichloro-benzene at 140 - 150℃; for 0.05h; Irradiation; Yields of byproduct given;	A 72% B n/a
With trichlorophosphate In 1,2-dichloro-benzene at 140 - 150℃; for 0.05h; microwave irradiation, other solvent, other time;	A 72% B n/a
With trichlorophosphate In toluene Irradiation;

3,4-dihydro-2H-isoquinoline-1-thione (6552-60-9) + phenylboronic acid (98-80-6) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate In tetrahydrofuran for 0.75h; Inert atmosphere; Reflux;	66%

nitrobenzene (98-95-3) + 1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + aniline (62-53-3)

Conditions	Yield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;	A 60% B 62%

1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8) + 2-methyl-5-nitroaniline (99-55-8) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + 4-methylbenzene-1,3-diamine (95-80-7)

Conditions	Yield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;	A 50% B 50%

1-(methylsulfanyl)-3,4-dihydroisoquinoline (14157-05-2) + 1,4-Phenyldiboronic acid (4612-26-4) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + 1,1'-benzene-1,4-diyldi-3,4-dihydroisoquinoline

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate In tetrahydrofuran Inert atmosphere; Reflux;	A 30% B 23%

[2-(trifluoromethylsulfonyloxy)ethyl]benzene (54448-36-1) + benzonitrile (100-47-0) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
In 1,2-dichloro-ethane at 80℃; for 12h;	29%

N-phenethyl-benzamidine; hydrochloride (55174-20-4) + nitrobenzene (98-95-3) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
With trichlorophosphate

2-phenylethyl chloride (622-24-2) + tin(IV) chloride (7646-78-8) + benzonitrile (100-47-0) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

aluminium trichloride (7446-70-0) + N-phenethylbenzamide (3278-14-6) + ligroine → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
man zersetzt mit Eiswasser;

tetrachloromethane (56-23-5) + N-phenethylbenzamide (3278-14-6) + P2O5 → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

benzoyl chloride (98-88-4) + (η-2,5-Ph2C4H2N)(Ph3P)2ReH2 → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83.3 percent / Et3N / CH2Cl2 / 4 h / 20 °C 2: 82.4 percent / P2O5; POCl3 / xylene / 3 h / Heating View Scheme

phenethylamine (64-04-0) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83.3 percent / Et3N / CH2Cl2 / 4 h / 20 °C 2: 82.4 percent / P2O5; POCl3 / xylene / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 92 percent / 10percent aq. NaOH / CH2Cl2 / 0.25 h 2: 1 g / POCl3, P2O5 / 2 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 91.5 percent / 15percent sodium hydroxide / H2O / 1 h / 0 °C 2: 94 percent / phosphorus pentachloride / benzene / 1 h / 0 °C 3: 96 percent / 1 h / 50 °C / 0.1 Torr 4: 97 percent / stannic chloride / CHCl3 / 100 h View Scheme

benzoyl chloride (98-88-4) + 6-t-butyl-12-p-tolyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azastibocine → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus oxychloride View Scheme

phenethylamine (64-04-0) + 4-[Ph2(AcO)2Bi]-C6H4-OCH2-polystyrene cross-linked with divinylbenzene → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus oxychloride View Scheme

Ethyl benzoyl carbonate (3741-66-0) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 20 - 60 °C 2: POCl3; P2O5 / xylene / 130 °C View Scheme

benzoic acid (65-85-0) + /PPFKE123-1965/ → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / dimethylformamide / 0.5 h / cooling 2: dimethylformamide / 20 - 60 °C 3: POCl3; P2O5 / xylene / 130 °C View Scheme

benzoyl chloride (98-88-4) + (S)-2-chloro-butyric acid → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / 10percent aq. NaOH / CH2Cl2 / 0.25 h 2: 1 g / POCl3, P2O5 / 2 h / Heating View Scheme

3,4-dihydroisoquinoline (3230-65-7) + β-phenethylamino-malonic acid bis-β-phenethylamine → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: 1.) NaHCO3, tert-butyl hypochlorite, 2.) KO2, 18-crown-6 ether / 1.) ether, 10 deg C, 2.) ether, 4.5 h View Scheme

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) → 1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8)

Conditions	Yield
With C42H64Cl4Ir2N6O4S2; H-Gly-NH2 In dimethyl sulfoxide at 30 - 50℃; for 18.25h; pH=7.8; Reagent/catalyst;	99%
With methanol; sodium tetrahydroborate at 25℃; for 2.5h;	99.2%
With sodium tetrahydroborate In methanol at 25℃; for 2.5h;	99.2%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) → (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8, 96719-89-0, 118864-75-8)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C42H46FeP2; hydrogen bromide; hydrogen In tetrahydrofuran; water at 30℃; under 38002.6 Torr; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Pressure; Schlenk technique; Autoclave; enantioselective reaction;	99%
With (S)-diopRuCl2(R)-p-Me-BIMAH; potassium tert-butylate; hydrogen In ethanol at 25 - 35℃; under 22801.5 Torr; Reagent/catalyst; Autoclave;	95%
With C27H29N3O6; trifluoroacetic acid In toluene at 30℃; for 24h; Reagent/catalyst; Temperature;	89%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + 2,3-diphenylcyclopropen-1-thione (2570-01-6) → 2,3,10b-Triphenyl-1-thioxo-1,5,6,10b-tetrahydropyrrolo<2.1-a>isochinolin (71611-98-8)

Conditions	Yield
In 1,2-dimethoxyethane at 20℃; for 15h;	95%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) → (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (180272-45-1)

Conditions	Yield
Stage #1: 1-phenyl-3,4-dihydroisoquinoline With N-Bromosuccinimide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate; (+)-(R)-[2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl]bis(diphenylphosphane) In 1,2-dichloro-ethane at 20℃; for 0.166667h; Stage #2: With hydrogen In 1,2-dichloro-ethane at 30℃; under 25858.1 Torr; for 24h; enantioselective reaction;	94%
With N-Bromosuccinimide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; sodium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In 1,2-dichloro-ethane at 30℃; under 25858.1 Torr; for 24h; Glovebox; enantioselective reaction;	94%
With N-Bromosuccinimide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; sodium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 30℃; under 25858.1 Torr; for 24h; Glovebox; enantioselective reaction;	94%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + p-toluenesulfonyl chloride (98-59-9) → (R)-(+)-2-(4-methylphenylsulfonyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (220936-57-2)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-3,5-diMe-Synphos; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In 1,4-dioxane at 40℃; under 7500.75 Torr; for 18h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	94%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + mercaptoacetic acid (68-11-1) → 10b-phenyl-5,6-dihydro-2H-thiazolo[2,3-a]isoquinolin-3-(10bH)-one (1547397-90-9)

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; chloroform at 20℃; for 1h;	93%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + triphenylsilylacetylene (6229-00-1) + methyl chloroformate (79-22-1) → (S)-methyl 1-phenyl-1-((triphenylsilyl)ethynyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Conditions	Yield
With copper(l) iodide; N-ethyl-N,N-diisopropylamine; 2,6-bis[(4R)-5,5-dihydro-4-phenyl-2-oxazolyl]pyridine In chloroform at 0 - 20℃; for 24h; Inert atmosphere; Sealed tube; enantioselective reaction;	91%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + Diphenylphosphine oxide (4559-70-0) → (2-(3,4-dihydroisoquinolin-1-yl)phenyl)diphenylphosphine oxide

Conditions	Yield
With potassium hexafluorophosphate; [Cp*Rh(OAc)2] In methanol at 65℃; Electrochemical reaction;	89%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + ethyl iodide (75-03-6) → 1-Phenyl-2-ethyl-3,4-dihydroisoquinolinium iodide

Conditions	Yield
In acetonitrile for 1h; Heating;	88.5%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + benzyl bromide (100-39-0) → 1-phenyl-2-benzyl-3,4-dihydroisoquinolinium bromide

Conditions	Yield
In acetonitrile for 1h; Heating;	88.3%
In acetonitrile for 8h; Reflux;	84%
In acetonitrile

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + silver trifluoroacetate (2966-50-9) + diphenyl acetylene (501-65-5) → C29H22N(1+)*C2F3O2(1-)

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In ethanol at 80℃; for 0.5h;	88%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In ethanol at 80℃; for 0.5h; Inert atmosphere;	88%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + diphenylcyclopropenone (886-38-4) → 2,3,10b-Triphenyl-1-oxo-1,5,6,10b-tetrahydropyrrolo<2.1-a>isochinolin (71611-93-3)

Conditions	Yield
In ethanol for 1h; Heating;	87%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + 5-decyne (1942-46-7) → C25H30N(1+)*C2F3O2(1-)

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; silver trifluoroacetate In ethanol for 40h; Reflux; Green chemistry; regioselective reaction;	85%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + methyl iodide (74-88-4) → 2-methyl-1-phenyl-3,4-dihydroisoquinolinium iodide (69311-06-4)

Conditions	Yield
In toluene for 3h; Heating;	84%
In acetonitrile for 1h; Heating;	75.5%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + acetic anhydride (108-24-7) → 2-(3,4-dihydroisoquinolin-1-yl)phenyl acetate (1408083-08-8)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; palladium diacetate In 1,2-dichloro-ethane at 80℃; for 3h;	82%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + N-phthaloylglycine (4702-13-0) → 2-(2-Oxo-9b-phenyl-1,4,5,9b-tetrahydro-2H-azeto[2,1-a]isoquinolin-1-yl)-isoindole-1,3-dione (96142-53-9)

Conditions	Yield
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20℃; for 8h;	80%

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + phenylacetonitrile (140-29-4) → 2-phenyl-1-(1-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)ethan-1-one

Conditions	Yield
Stage #1: 1-phenyl-3,4-dihydroisoquinoline; phenylacetonitrile With manganese; chloro-trimethyl-silane; bis(cyclopentadienyl)titanium(IV) diphenoxide; triethylamine hydrochloride In tetrahydrofuran at 60℃; for 48h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether; dichloromethane Cooling; regioselective reaction;	78%

methanol (67-56-1) + 1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + 2,3-diphenylcyclopropen-1-thione (2570-01-6) → 2-Methoxy-3,4,11b-triphenyl-7,11b-dihydro-2H,6H-<1.3>thiazino<2.3-a>isochinolin (71612-04-9)

Conditions	Yield
Heating;	76%
for 2h; Heating;

methanol (67-56-1) + 1-phenyl-3,4-dihydroisoquinoline (52250-50-7) → 1-(2'-methoxylphenyl)-3,4-dihydroisoquinoline (803636-11-5)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; palladium diacetate for 3h; Reflux;	76%

Upstream product

• 55174-20-4 N-phenethyl-benzamidine; hydrochloride 
• 98-95-3 nitrobenzene 
• 60943-13-7 N-(2-phenethyl)benzimidoyl chloride 
• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 3278-14-6 N-phenethylbenzamide 
• 98-88-4 benzoyl chloride 
• 64-04-0 phenethylamine 
• 99-55-8 2-methyl-5-nitroaniline 
• 65-85-0 benzoic acid 
• 1196-38-9 3,4-dihydroisoquinolin-1(2H)-one 
• 100-58-3 phenylmagnesium bromide 
• 78105-68-7 2-(2-bromophenyl)-2-phenyl-1,3-dioxolane 
• 92059-93-3 2-bromobenzophenone oxime 
• 6552-60-9 3,4-dihydro-2H-isoquinoline-1-thione 

Downstream Products

• 33674-82-7 7-nitro-1-phenyl-3,4-dihydro-isoquinoline 
• 22990-19-8 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 180272-45-1 (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 583871-59-4 1-Hydroxy-2-methyl-1-phenyl-1,2,3,4-tetrahydroisochinolin 
• 869884-00-4 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline tartarate 
• 3297-72-1 1-phenylisoquinoline 
• 86448-84-2 N-oxy phenyl-1 dihydro-3,4-isoquinoleine 
• 88333-47-5 5',6'-Dihydro-10b'-phenylspiroisochinolin>-2',3'-dicarbonitril 
• 71611-93-3 2,3,10b-Triphenyl-1-oxo-1,5,6,10b-tetrahydropyrrolo<2.1-a>isochinolin 
• 96719-81-2 2-(2-Phenoxy-ethyl)-1-phenyl-3,4-dihydro-isoquinolinium; bromide 
• 96142-53-9 2-(2-Oxo-9b-phenyl-1,4,5,9b-tetrahydro-2H-azeto[2,1-a]isoquinolin-1-yl)-isoindole-1,3-dione 
• 70454-07-8 1-Phenoxy-9b-phenyl-1,4,5,9b-tetrahydro-azeto[2,1-a]isoquinolin-2-one 
• 104576-32-1 1-(1-phenylisoquinolin-2(1H)-yl)ethan-1-one 
• 88252-51-1 1-(4-Chloro-phenoxy)-9b-phenyl-1,4,5,9b-tetrahydro-azeto[2,1-a]isoquinolin-2-one 

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Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues

A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.

Diprotonative stabilization of ring-opened carbocationic intermediates: conversion of tetrahydroisoquinoline to triarylmethanes

Superacid-promoted conversion of tetrahydroisoquinolines to triarylmethanes via tandem reactions of C-N bond scission, Friedel-Crafts alkylation, C-O bond scission, and electrophilic aromatic amidation was developed. Dication formation was important for stabilizing the ring-opened carbocationic intermediate, which is a new role for diprotonation in reaction mechanisms. This journal is