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

HRID 49185

反応式

HRID 49185 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-25a6346f6a0b46519b1f9908d027fc48
出典データセット
uspto-grants-2004_03
特許番号
US06706732B1

関連ノート

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