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3,4-Dihydro-7-hydroxy-2(1H)-quinolinone
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Name

3,4-Dihydro-7-hydroxy-2(1H)-quinolinone

 EINECS N/A
CAS No. 22246-18-0 Density 1.282 g/cm3
PSA 49.33000 LogP 1.41490
Solubility N/A Melting Point 233-237 °C
Formula C9H9NO2 Boiling Point 403.7 °C at 760 mmHg
Molecular Weight 163.176 Flash Point 198 °C
Transport Information N/A Appearance Pale yellow powder
Safety S36/37 Risk Codes 22-43
Molecular Structure Molecular Structure of 22246-18-0 (3,4-Dihydro-7-hydroxy-2(1H)-quinolinone) Hazard Symbols HarmfulXn, IrritantXi
Synonyms

3,4-Dihydrogen-7-Hydroxy-2(1H)-Quinolinone;7-Hydroxy-3,4-dihydro-2(1H)Quinolineone;7-Hydroxy-3,4-Dihydro-2(1H)Quinoliunone;2(1H)-Quindinone,3,4-dohydro-7Hydroxy;7-Hydroxy-3,4-dihydro-2-quinolinone;7-Hydroxy-3,4-dihydro-2(1H)Quinolinone;7-(4-bromo-butoxy)-3,4-dihydro-1H-quinolin-2-one;7-hydroxy-3,4-dihydroquinazolone;7-Hydroxy-3,4-dihydro-1H-quinolin-2-one;3,4-dihydro-7-hydroxycarbostyril;7-Hydroxy-1,2,3,4-tetrahydro-2-quinolinone;7-hydroxy-3, 4-dihydro-2 (1H)-quinolinone;7-Hydroxy-2-Oxo-3,4-Dihydroquinoline;

Article Data 28

3,4-Dihydro-7-hydroxy-2(1H)-quinolinone Synthetic route

50297-40-0

3-chloro-N-(3-hydroxyphenyl)propanamide

22246-18-0

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone

Conditions
ConditionsYield
With aluminum (III) chloride In N,N-dimethyl-formamide at 90 - 150℃; for 6h; Cooling with ice;88%
Stage #1: 3-chloro-N-(3-hydroxyphenyl)propanamide With aluminum (III) chloride at 210℃; for 0.5h;
Stage #2: With water at 20℃;		76%
With aluminum (III) chloride In N,N-dimethyl acetamide at 130 - 140℃;68%
21261-76-7

3-chloro-N-(3-methoxyphenyl)propionamide

22246-18-0

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone

Conditions
ConditionsYield
aluminum (III) chloride In N,N-dimethyl acetamide at 140 - 150℃; for 2.75h; Friedel Crafts Alkylation;82%
With aluminium trichloride; N,N-dimethyl acetamide at 150 - 160℃; for 2h; Friedel-Crafts reaction;61.5%
With aluminum (III) chloride In N,N-dimethyl acetamide at 0 - 150℃; for 2h;54%
1127347-52-7

C9H7NO5

22246-18-0

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone

Conditions
ConditionsYield
With ammonium formate on silica gel; zinc In carbon dioxide at 50℃; under 90009 Torr; Autoclave; liquid CO2;78%

4-benyzloxy-2-nitrobenzenediazonium tetrafluoroborate

292638-85-8

acrylic acid methyl ester

22246-18-0

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone

Conditions
ConditionsYield
Stage #1: 4-benyzloxy-2-nitrobenzenediazonium tetrafluoroborate; acrylic acid methyl ester With palladium diacetate In 1,4-dioxane at 25℃; for 6h; Heck reduction-cyclisation-debenzylation reaction;
Stage #2: With hydrogen; palladium diacetate; pyrographite In 1,4-dioxane at 50℃; for 24h; Heck reduction-cyclisation-debenzylation reaction;		66%
21261-76-7

3-chloro-N-(3-methoxyphenyl)propionamide

A

22246-18-0

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone

B

30389-33-4

5-hydroxycarbostyril

Conditions
ConditionsYield
Stage #1: N-(3-methoxyphenyl)-3-chloropropionamide; aluminum (III) chloride at 155 - 165℃; for 4h;
Stage #2: With methanol; sodium hydroxide In water at 20℃; for 1h; pH=7; Product distribution / selectivity; Heating / reflux;		A 62.3%
B n/a
Stage #1: N-(3-methoxyphenyl)-3-chloropropionamide With N,N-dimethyl acetamide; aluminum (III) chloride In water at 95 - 165℃; for 5.5h;
Stage #2: With methanol; sodium hydroxide In water at 20℃; for 1h; pH=7; Product distribution / selectivity; Heating / reflux;		A 61.3%
B n/a
Stage #1: N-(3-methoxyphenyl)-3-chloropropionamide; aluminum (III) chloride In water at 95 - 165℃; for 5.5h;
Stage #2: With methanol; sodium hydroxide In water at 20℃; for 1h; pH=7; Product distribution / selectivity; Heating / reflux;		A 61.3%
B n/a
aluminum chloride powder

aluminum chloride powder

21261-76-7

3-chloro-N-(3-methoxyphenyl)propionamide

22246-18-0

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone

Conditions
ConditionsYield
In ice-H2O55%
22246-17-9

7-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline

22246-18-0

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone

Conditions
ConditionsYield
With hydrogen bromide
50297-40-0

3-chloro-N-(3-hydroxyphenyl)propanamide

A

22246-18-0

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone

B

5-hydroxy-3,4-dihydro-1H-quinolin-2-one

5-hydroxy-3,4-dihydro-1H-quinolin-2-one

Conditions
ConditionsYield
With aluminium trichloride beim Schmelzen;
536-90-3

m-Anisidine

22246-18-0

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / NaHCO3 / CH2Cl2 / 4 h / 20 °C
2: 61.5 percent / N,N-dimethylacetamide; aluminium trichloride / 2 h / 150 - 160 °C
View Scheme
Multi-step reaction with 2 steps
1: 95 percent / aq. K2CO3 / acetone / 1 h / 0 °C
2: 4 percent / AlCl3 / chlorobenzene / 6 h / 120 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium carbonate / toluene / 2 h / 40 - 65 °C
2: aluminum (III) chloride / N,N-dimethyl acetamide / 140 - 150 °C
View Scheme
Multi-step reaction with 2 steps
1: pyridine / tetrahydrofuran / 0 - 20 °C
2: aluminum (III) chloride; N,N-dimethyl acetamide / 4 h / 140 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / toluene / 2 h / 50 °C
2: aluminum (III) chloride / N,N-dimethyl acetamide / 2 h / 0 - 150 °C
View Scheme
103986-96-5

methyl (E)-3-(4′-methoxy-2′-nitrophenyl)acrylate

22246-18-0

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Raney nickel; ethanol / Hydrogenation
2: aqueous hydrobromic acid
View Scheme

3,4-Dihydro-7-hydroxy-2(1H)-quinolinone Chemical Properties

Molecular Structure of 3,4-Dihydro-7-hydroxy-2(1H)-quinolinone (CAS NO.22246-18-0):

IUPAC Name: 7-hydroxy-3,4-dihydro-1H-quinolin-2-one
Molecular formula: C9H9NO2
Molar weight: 163.17
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 29.54 Å2
Index of Refraction: 1.604
Molar Refractivity: 43.78 cm3
Molar Volume: 127.2 cm3
Surface Tension: 51.7 dyne/cm
Density: 1.282 g/cm3
Flash Point: 198 °C
Enthalpy of Vaporization: 68.06 kJ/mol
Boiling Point: 403.7 °C at 760 mmHg
Vapour Pressure: 4.28E-07 mmHg at 25°C
Melting point: 233-237 °C
Appearance: Pale Yellow Powder
Product Categories: Quinolines, Quinazolines and derivatives; Quinoline derivatives; Intermediatesofaripiprazole; Aromatics Compounds; Intermediates of Aripiprazole; Aromatics; Intermediates & Fine Chemicals; Pharmaceuticals
SMILES: O=C2Nc1cc(O)ccc1CC2
InChI: InChI=1/C9H9NO2/c11-7-3-1-6-2-4-9(12)10-8(6)5-7/h1,3,5,11H,2,4H2,(H,10,12)

3,4-Dihydro-7-hydroxy-2(1H)-quinolinone Safety Profile

Hazard Codes: HarmfulXn,IrritantXi
The Risk Statements information:
22:  Harmful if swallowed 
43:  May cause sensitization by skin contact 
The Safety Statements information:
36/37:  Wear suitable protective clothing and gloves 

3,4-Dihydro-7-hydroxy-2(1H)-quinolinone Specification

  3,4-Dihydro-7-hydroxy-2(1H)-quinolinone , with CAS number of 22246-18-0, can be called 3,4-Dihydrogen-7-Hydroxy-2(1H)-Quinolinone ; 7-Hydroxy-3,4-dihydro-2(1H)Quinolineone ; 2(1H)-Quindinone,3,4-dohydro-7Hydroxy ; 7-(4-bromo-butoxy)-3,4-dihydro-1H-quinolin-2-one ; 7-Hydroxy-1,2,3,4-tetrahydro-2-quinolinone ; 7-Hydroxy-1,2,3,4-tetrahydroquinoline ; 3,4-dihydro-7-hydroxy quinolin-2(1H)-one . It is a pale yellow powder.

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