Butyn-2-one → 2-Methyl-7-(2-methylphenyl)-5,6,7,8-tetrahydroquinolin-5-one

HRID 1700517노트

반응식

HRID 1700517 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=O)[CH2:11][C:10](=[O:15])[CH2:9]1.C([O-])(=O)C.[NH4+:20].[CH3:21][C:22](=O)[C:23]#[CH:24]>C(O)C>[CH3:21][C:22]1[CH:23]=[CH:24][C:11]2[C:10](=[O:15])[CH2:9][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])[CH2:13][C:12]=2[N:20]=1

참가 물질

5

반응물 3

HCID 15018Butyn-2-oneHCID 517165Ammonium AcetateHCID 176065755-(2-Methylphenyl)cyclohexane-1,3-dione

생성물 1

HCID 183174432-Methyl-7-(2-methylphenyl)-5,6,7,8-tetrahydroquinolin-5-one수율 55.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 5-(2-methylphenyl)cyclohexane-1,3-dione (1.3 g) and ammonium acetate (0.49 g) in ethanol (30 ml) was stirred at room temperature for 30 minutes, and to the mixture was added 3-butyn-2-one (0.44 g). The reaction solution was stirred at room temperature for 1.5 hours and refluxed for 27 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with sodium hydrogen carbonate solution, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) to give colorless crystals of 2-methyl-7-(2-methylphenyl)-5,6,7,8-tetrahydroquinolin-5-one (0.88 g).

후처리

  1. stirringThe reaction solution was stirred at room temperature for 1.5 hours
  2. temperaturerefluxed for 27 hours
  3. customUnder reduced pressure, the solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe solution was washed with sodium hydrogen carbonate solution, water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)

출처 및 근거

ORD 기록
ord-787307b5c6be41d0ba097f817d6fa563
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350749B1

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