Potassium Hydroxide → 7-(2-Chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one

HRID 49185

Reaction equation

HRID 49185 reaction equation
[NH2:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[CH2:5][C:4](=[O:15])[CH:3]=1.CO[CH:18](OC)[CH2:19][C:20](=O)[CH3:21].[OH-].[K+]>C(O)C.C1(C)C=CC=CC=1>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH:6]1[CH2:7][C:2]2[N:1]=[CH:18][CH:19]=[C:20]([CH3:21])[C:3]=2[C:4](=[O:15])[CH2:5]1

Participants

6

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 2285484,4-Dimethoxy-2-butanoneHCID 98593161-Amino-5-(2-chlorophenyl)cyclohexen-3-one

Product 1

HCID 110655617-(2-Chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneYield 75.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 1-amino-5-(2-chlorophenyl)cyclohexen-3-one (2.7 g) in ethanol (50 ml) and toluene (150 m) was combined with acetyl acetoaldehyde dimethyl acetal (4.0 g) and 85% potassium hydroxide (0.67 g), and the mixture was heated under reflux. 85% Potassium hydroxide (0.14 g) was added three times at an interval of 30 minutes, and then heated under reflux further for 1 hour. The solvent was distilled off under reduced pressure, and the residue was combined with ethyl acetate, washed successively with water and saturated brine, and dried over magnesium sulfate. After concentrating under reduced pressure, the residue was subjected to a column chromatography on a silica gel (EtOAc-hexane) to obtain 7-(2-chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (2.5 g) as a crystal. Melting point and NMR data were in agreement with those of the compound obtained in Reference Example 2.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperatureheated
  4. temperatureunder reflux further for 1 hour
  5. distillationThe solvent was distilled off under reduced pressure
  6. washwashed successively with water and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationAfter concentrating under reduced pressure

Sources & evidence

ORD record
ord-25a6346f6a0b46519b1f9908d027fc48
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Linked notes

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