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

HRID 1700479노트

반응식

HRID 1700479 반응식
[NH2:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[CH2:5][C:4](=[O:16])[CH:3]=1.[OH-].[K+]>C(O)C.C1(C)C=CC=CC=1>[CH3:15][C:9]1[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=1[CH:6]1[CH2:7][C:2]2[N:1]=[CH:7][CH:2]=[C:3]([CH3:4])[C:3]=2[C:4](=[O:16])[CH2:5]1

참가 물질

5

반응물 2

HCID 14797Potassium Hydroxide2회HCID 183175811-Amino-5-(2,5-dimethylphenyl)cyclohexen-3-one

생성물 1

HCID 183173177-(2,5-Dimethylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one수율 130.8%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 1140Toluene용매

반응 조건

온도
115 °C

실험 절차

In a mixture of ethanol (35 ml) and toluene (90 ml) was dissolved 1-amino-5-(2,5-dimethylphenyl)cyclohexen-3-one (1.7 g), and to the solution were added 3-oxobutylaldehydedimethylacetal (2.66 g) and granulated potassium hydroxide (440 mg). The mixture was stirred at 115° C. (bath temperature), and to the mixture was added granulated potassium hydroxide (90 mg), 30 minutes later; 1 hour later; and 1.5 hours, respectively. The reaction solution was stirred at the same temperature for 1 hour and cooled. Under reduced pressure, the solvent was evaporated, and to the residue were added ethyl acetate (40 ml) and water (20 ml). The mixture was shaken and separated ethyl acetate layer was washed with brine. Under reduced pressure, ethyl acetate was evaporated, and the residue was purified with silica gel column chromatography (EtOAc/hexane) and eluted with ethyl acetate/hexane to give 7-(2,5-dimethylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.37 g) as colorless crystals.

후처리

  1. custom1 hour
  2. custom1.5 hours
  3. stirringThe reaction solution was stirred at the same temperature for 1 hour
  4. temperaturecooled
  5. customUnder reduced pressure, the solvent was evaporated
  6. additionto the residue were added ethyl acetate (40 ml) and water (20 ml)
  7. stirringThe mixture was shaken
  8. customseparated ethyl acetate layer
  9. washwas washed with brine
  10. customUnder reduced pressure, ethyl acetate was evaporated
  11. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)
  12. washeluted with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-8ba522bf3218489c807ae851a5a1a4bc
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350749B1

반응 노트

불러오는 중…