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

HRID 49185

반응식

HRID 49185 반응식
[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

참가 물질

6

반응물 3

HCID 14797Potassium Hydroxide2회HCID 2285484,4-Dimethoxy-2-butanoneHCID 98593161-Amino-5-(2-chlorophenyl)cyclohexen-3-one

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-25a6346f6a0b46519b1f9908d027fc48
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706732B1

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