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

HRID 1700517ノート

反応式

HRID 1700517 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-787307b5c6be41d0ba097f817d6fa563
出典データセット
uspto-grants-2002_02
特許番号
US06350749B1

反応ノート

読み込み中…