Product Name

  • Name

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

  • EINECS
  • CAS No. 22246-18-0
  • Article Data28
  • CAS DataBase
  • Density 1.282 g/cm3
  • Solubility
  • 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
  • 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;
  • PSA 49.33000
  • LogP 1.41490

Synthetic route

3-chloro-N-(3-hydroxyphenyl)propanamide
50297-40-0

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

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
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%
3-chloro-N-(3-methoxyphenyl)propionamide
21261-76-7

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

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
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%
C9H7NO5
1127347-52-7

C9H7NO5

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

4-benyzloxy-2-nitrobenzenediazonium tetrafluoroborate

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
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%
3-chloro-N-(3-methoxyphenyl)propionamide
21261-76-7

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

A

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

B

5-hydroxycarbostyril
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

3-chloro-N-(3-methoxyphenyl)propionamide
21261-76-7

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

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

Conditions
ConditionsYield
In ice-H2O55%
7-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline
22246-17-9

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

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

Conditions
ConditionsYield
With hydrogen bromide
3-chloro-N-(3-hydroxyphenyl)propanamide
50297-40-0

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

A

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
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;
m-Anisidine
536-90-3

m-Anisidine

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
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
methyl (E)-3-(4′-methoxy-2′-nitrophenyl)acrylate
103986-96-5

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

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
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
2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

4-hydroxy-2-nitrobenzenediazonium tetrafluoroborate

4-hydroxy-2-nitrobenzenediazonium tetrafluoroborate

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

Conditions
ConditionsYield
Stage #1: 4-hydroxy-2-nitrobenzenediazonium tetrafluoroborate; acrylic acid methyl ester With sodium acetate; palladium diacetate In methanol at 20℃; for 12h; Mizoroki-Heck reaction; Inert atmosphere;
Stage #2: With hydrogen; pyrographite In methanol at 20℃; under 750.075 Torr; for 24h;
Stage #3: With hydrogenchloride In methanol; water		360 mg
N-(4-hydroxy-2-nitrophenyl)-acetamide
7403-75-0

N-(4-hydroxy-2-nitrophenyl)-acetamide

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: boron trifluoride - methanol (1/1) / methanol / 5 h / Inert atmosphere; Reflux
1.2: 0.33 h / -15 - 0 °C
2.1: sodium acetate; palladium diacetate / methanol / 12 h / 20 °C
3.1: pyrographite; hydrogen / methanol / 24 h / 750.08 Torr
View Scheme
C10H9NO5

C10H9NO5

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

Conditions
ConditionsYield
With hydrogen; pyrographite In methanol under 750.075 Torr; for 24h;360 mg
m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / acetonitrile / 0 °C
2: aluminum (III) chloride / dichloromethane
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / 2 h / 25 °C / pH 9
2: boron trifluoride diethyl etherate / toluene / 2 h / 60 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydrogencarbonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
1.2: 2 h / 20 °C / Inert atmosphere
2.1: aluminum (III) chloride / N,N-dimethyl acetamide / 4 h / 70 - 140 °C
View Scheme
C9H11NO3

C9H11NO3

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In toluene at 60℃; for 2h; Temperature;
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

7-(tert-butyl-dimethylsilanyloxy)-3,4-dihydro-1H-quinolin-2-one
1427053-51-7

7-(tert-butyl-dimethylsilanyloxy)-3,4-dihydro-1H-quinolin-2-one

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0℃;99.4%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

7-hydroxy-1,2,3,4-tetrahydroquinoline
58196-33-1

7-hydroxy-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran Inert atmosphere; Cooling with ice; Reflux;98%
With sodium tetrahydroborate In tetrahydrofuran at 0℃; Reflux;98%
With lithium aluminium tetrahydride In tetrahydrofuran Cooling with ice; Reflux;95%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

1-bromomethyl-3-chlorobenzene
766-80-3

1-bromomethyl-3-chlorobenzene

7-((3-chlorobenzyl)oxy)-3,4-dihydroquinolin-2(1H)-one
1458219-01-6

7-((3-chlorobenzyl)oxy)-3,4-dihydroquinolin-2(1H)-one

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 60℃; for 18h;97%
With potassium carbonate In acetonitrile for 8h; Reflux;68%
With potassium hydroxide In ethanol for 5h; Reflux;32%
4-chlorobutyl bromide
6940-78-9

4-chlorobutyl bromide

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

7-(4-chlorobutoxy)-3,4-dihydroquinoline-2(1H)-one
120004-79-7

7-(4-chlorobutoxy)-3,4-dihydroquinoline-2(1H)-one

Conditions
ConditionsYield
With lithium hydroxide In water; N,N-dimethyl-formamide at 40 - 50℃; for 3h; Reagent/catalyst; Solvent; Sealed tube; Large scale;95%
With potassium carbonate; polyethylene glycol-400 In water; acetone at 20℃; for 15.1667 - 16.1667h;94%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 30℃; for 24h; Solvent; Temperature; Large scale;93.2%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

2-Bromo-2'-acetonaphthone
613-54-7

2-Bromo-2'-acetonaphthone

7-[2-(naphthalen-2-yl)-2-oxoethoxy]-3,4-dihydroquinolin-2(1H)-one
1303566-73-5

7-[2-(naphthalen-2-yl)-2-oxoethoxy]-3,4-dihydroquinolin-2(1H)-one

Conditions
ConditionsYield
Stage #1: 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 2-Bromo-2'-acetonaphthone In N,N-dimethyl-formamide at 20℃; for 24h;		95%
Stage #1: 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 2-Bromo-2'-acetonaphthone In N,N-dimethyl-formamide at 20℃; for 24h;		88%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

4-chlorobutanal dimethyl acetal
29882-07-3

4-chlorobutanal dimethyl acetal

7-(4,4-dimethoxybutoxy)-3,4-dihydro-1H-quinolin-2-one
1359159-57-1

7-(4,4-dimethoxybutoxy)-3,4-dihydro-1H-quinolin-2-one

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In dimethyl sulfoxide at 115℃; for 4h;95%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

7-hydroxy-1H-quinolin-2-one
70500-72-0

7-hydroxy-1H-quinolin-2-one

Conditions
ConditionsYield
With palladium 10% on activated carbon; water; oxygen; acetic acid at 110 - 116℃; for 18h; Reagent/catalyst; Temperature;94.2%
With palladium 10% on activated carbon In decalin at 180℃; for 8h;90.9%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 66℃; for 4h; Catalytic behavior; Concentration; Solvent; Temperature;89%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

7-(4-methoxybenzoyloxy)-3,4-dihydro-1H-quinolin-2-one

7-(4-methoxybenzoyloxy)-3,4-dihydro-1H-quinolin-2-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 5h;93.3%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

1,4-dichlorobutane-d8

1,4-dichlorobutane-d8

C13H8(2)H8ClNO2

C13H8(2)H8ClNO2

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; for 3h; Inert atmosphere;92%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

C14H19Cl3N2*ClH

C14H19Cl3N2*ClH

aripiprazole
129722-12-9

aripiprazole

Conditions
ConditionsYield
With potassium carbonate In water at 99℃; for 5h; Reagent/catalyst; Temperature;91.4%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone
129722-34-5

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

Conditions
ConditionsYield
Stage #1: 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone With potassium carbonate In water; acetone at 20℃; for 1h;
Stage #2: 1,4-dibromo-butane In water; acetone at 20℃; for 16h;		91%
With potassium iodide; sodium hydroxide In acetonitrile at 30℃; for 16h;85%
With sodium hydroxide In ethanol for 2.5h; Heating;83%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

1,4-dichlorobutane
110-56-5

1,4-dichlorobutane

7-(4-chlorobutoxy)-3,4-dihydroquinoline-2(1H)-one
120004-79-7

7-(4-chlorobutoxy)-3,4-dihydroquinoline-2(1H)-one

Conditions
ConditionsYield
With potassium carbonate In propan-1-ol for 8 - 10h; Product distribution / selectivity; Heating / reflux;91%
With potassium carbonate; sodium sulfate; Aliquat 336 In toluene for 14h; Product distribution / selectivity; Heating / reflux;75%
With potassium carbonate In ISOPROPYLAMIDE at 90 - 95℃; for 15 - 16h;75%
With potassium carbonate In acetonitrile for 22h; Product distribution / selectivity; Heating / reflux;74%
With potassium carbonate In propan-1-ol; isopropyl alcohol for 19h; Product distribution / selectivity; Heating / reflux;66%
1 ,6-dibromohexane
629-03-8

1 ,6-dibromohexane

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

7-((6-bromohexyl)oxy)-3,4-dihydroquinolin-2(1H)-one
1303529-03-4

7-((6-bromohexyl)oxy)-3,4-dihydroquinolin-2(1H)-one

Conditions
ConditionsYield
Stage #1: 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone With potassium carbonate In water; acetone at 20℃; for 1h;
Stage #2: 1 ,6-dibromohexane In water; acetone at 20℃; for 16h;		91%
With potassium carbonate In acetonitrile at 60 - 65℃; Inert atmosphere;56.8%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone
129722-34-5

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

7-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-7-oxy)butoxy)-3,4-dihydroquinoline-2(1H)-one

7-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-7-oxy)butoxy)-3,4-dihydroquinoline-2(1H)-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;90.9%
Stage #1: 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone With sodium hydroxide In methanol for 2h; Heating;
Stage #2: 7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone In N,N-dimethyl-formamide at 20℃; Further stages.;		16.8 g
With potassium hydroxide In ethanol Reflux;
1,5-dibromo-pentane
111-24-0

1,5-dibromo-pentane

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

7-((5-bromopentyl)oxy)-3,4-dihydroquinolin-2(1H)-one
63309-41-1

7-((5-bromopentyl)oxy)-3,4-dihydroquinolin-2(1H)-one

Conditions
ConditionsYield
Stage #1: 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone With potassium carbonate In water; acetone at 20℃; for 1h;
Stage #2: 1,5-dibromo-pentane In water; acetone at 20℃; for 16h;		90%
With potassium carbonate In acetonitrile at 60 - 65℃; Inert atmosphere;60.2%
With potassium hydroxide In isopropyl alcohol for 4h; Heating;53%
With potassium carbonate In acetonitrile at 50℃; for 20h;
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

methyl iodide
74-88-4

methyl iodide

7-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline
22246-17-9

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

Conditions
ConditionsYield
Stage #1: 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone With potassium carbonate In isopropyl alcohol at 20℃; for 0.5h; Inert atmosphere;
Stage #2: methyl iodide In isopropyl alcohol for 60h; Reflux;		90%
In N,N-dimethyl-formamide at 20℃;82%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 18h;63%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

7-(3-bromopropoxy)-3,4-dihydroquinolin-2(1H)-one
82657-32-7

7-(3-bromopropoxy)-3,4-dihydroquinolin-2(1H)-one

Conditions
ConditionsYield
Stage #1: 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone With potassium carbonate In water; acetone at 20℃; for 1h;
Stage #2: 1,3-dibromo-propane In water; acetone at 20℃; for 16h;		90%
With potassium carbonate In ethanol Reflux;88%
With potassium carbonate In acetonitrile at 60 - 65℃; Inert atmosphere;65.3%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

t-butyl 4-(2-nitrophenylsulfonyloxy)piperidine-1-carboxylate
1092366-87-4

t-butyl 4-(2-nitrophenylsulfonyloxy)piperidine-1-carboxylate

tert-butyl 4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]piperidine-1-carboxylate
583031-07-6

tert-butyl 4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]piperidine-1-carboxylate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 7h; Williamson Synthesis;87%
With triethylamine In dichloromethane
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

6-bromo-7-hydroxy-3,4-dihydro-1H-quinolin-2-one
1194459-28-3

6-bromo-7-hydroxy-3,4-dihydro-1H-quinolin-2-one

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 9h;87%
With N-Bromosuccinimide58%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃;0.82 g
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2-oxo-1,2,3,4-tetrahydroquinolin-7-yl trifluoromethanesulfonate
882023-50-9

2-oxo-1,2,3,4-tetrahydroquinolin-7-yl trifluoromethanesulfonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 10 - 30℃; for 3h;85%
Stage #1: 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone With pyridine In chloroform at 20℃; for 0.166667h;
Stage #2: trifluoromethylsulfonic anhydride In chloroform at 20℃; for 1.5h; Cooling with ice;		67%
Stage #1: 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone With pyridine In chloroform at 0 - 40℃; for 0.166667h;
Stage #2: trifluoromethylsulfonic anhydride In chloroform at 10 - 15℃; for 1.58333h;
With pyridine In chloroform at 0 - 23℃; for 18h; Inert atmosphere; Schlenk technique;
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

α-bromoacetophenone
70-11-1

α-bromoacetophenone

3,4-dihydro-7-(2-oxo-2-phenylethoxy)quinolin-2(1H)-one

3,4-dihydro-7-(2-oxo-2-phenylethoxy)quinolin-2(1H)-one

Conditions
ConditionsYield
Stage #1: 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; deprotonation;
Stage #2: α-bromoacetophenone In N,N-dimethyl-formamide at 20℃; for 24h; Alkylation;		84%
With potassium carbonate
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

benzyl bromide
100-39-0

benzyl bromide

7-(benzyloxy)-3,4-dihydro-2(1H)-quinolinone
92962-89-5

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

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 16h;84%
With potassium carbonate In acetonitrile Heating;79%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;67%
With potassium hydroxide In ethanol for 5h; Reflux;57%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

(4-bromobutoxy)-tert-butyldimethylsilane
89043-32-3

(4-bromobutoxy)-tert-butyldimethylsilane

7-(4-((tert-butyldimethylsilyl)oxy)butoxy)-3,4-dihydroquinolin-2(1H)-one

7-(4-((tert-butyldimethylsilyl)oxy)butoxy)-3,4-dihydroquinolin-2(1H)-one

Conditions
ConditionsYield
With potassium carbonate In ethanol Reflux;84%
With potassium carbonate; potassium iodide Reflux;84%
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

2-Bromo-4'-phenylacetophenone
135-73-9

2-Bromo-4'-phenylacetophenone

7-[2-(1,1'-biphenyl-4-yl)-2-oxoethoxy]-3,4-dihydroquinolin-2(1H)-one

7-[2-(1,1'-biphenyl-4-yl)-2-oxoethoxy]-3,4-dihydroquinolin-2(1H)-one

Conditions
ConditionsYield
Stage #1: 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; deprotonation;
Stage #2: 2-Bromo-4'-phenylacetophenone In N,N-dimethyl-formamide at 20℃; for 24h; Alkylation;		80%
With potassium carbonate
4-chlorobutyl bromide
6940-78-9

4-chlorobutyl bromide

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

A

7-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-7-oxy)butoxy)-3,4-dihydroquinoline-2(1H)-one

7-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-7-oxy)butoxy)-3,4-dihydroquinoline-2(1H)-one

B

7-(4-chlorobutoxy)-3,4-dihydroquinoline-2(1H)-one
120004-79-7

7-(4-chlorobutoxy)-3,4-dihydroquinoline-2(1H)-one

Conditions
ConditionsYield
With sodium hydroxide In ISOPROPYLAMIDE at 36 - 40℃; for 4h; Product distribution / selectivity;A 0.3%
B 80%
...Expand
7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

N,N-diethylcarbamyl chloride
88-10-8

N,N-diethylcarbamyl chloride

2-oxo-1,2,3,4-tetrahydroquinolin-7-yl diethylcarbamate

2-oxo-1,2,3,4-tetrahydroquinolin-7-yl diethylcarbamate

Conditions
ConditionsYield
With pyridine for 12h; Reflux;80%
2-(morpholin-4-yl)ethanol
622-40-2

2-(morpholin-4-yl)ethanol

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

7-(2-morpholinoethoxy)-3,4-dihydroquinolin-2(1H)-one
1609210-11-8

7-(2-morpholinoethoxy)-3,4-dihydroquinolin-2(1H)-one

Conditions
ConditionsYield
With cyanomethylenetributyl-phosphorane In toluene at 100℃; for 16h; Mitsunobu Displacement;80%
2-(4-methylpiperazinyl)ethanol
5464-12-0

2-(4-methylpiperazinyl)ethanol

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone
22246-18-0

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

7-[2-(4-methylpiperazin-1-yl)ethoxy]-3,4-dihydroquinolin-2(1H)-one

7-[2-(4-methylpiperazin-1-yl)ethoxy]-3,4-dihydroquinolin-2(1H)-one

Conditions
ConditionsYield
With cyanomethylenetributyl-phosphorane In toluene at 100℃; for 16h; Mitsunobu Displacement;80%

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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