Water → 2-Cyclohexyloxy-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one hydrochloride

HRID 1817817ノート

反応式

HRID 1817817 の反応式
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na].[Cl:9][C:10]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[CH2:15][C:14]([CH3:22])([CH3:21])[CH2:13][C:12]=2[N:11]=1.O>C(OCC)C>[ClH:9].[CH:1]1([O:7][C:10]2[CH:19]=[CH:18][C:17]3[C:16](=[O:20])[CH2:15][C:14]([CH3:22])([CH3:21])[CH2:13][C:12]=3[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 962WaterHCID 7966CyclohexanolHCID 5360545SodiumHCID 148125452-Chloro-7,7-dimethyl-7,8-dihydroquinolin-5(6H)-one

生成物 1

HCID 690420072-Cyclohexyloxy-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one hydrochloride収率 90.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution of cyclohexanol (0.2 g, 2.0 mmol) in diethyl ether (10 ml) was added sodium (0.035 g, 1.5 mmol) and it was stirred at room temperature for 2.5 h. Then 2-chloro-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one (0.21 g, 1.0 mmol) was added and the resulting mixture was stirred at 30° C. for 24 h. Water (12 ml) was added and the mixture was extracted with ethyl acetate (2×10 ml). The organic phase was washed with water (10 ml) and dried over magnesium sulphate, then it was filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (petroleum ether-ethyl acetate, 10:1) followed by treatment with a dry 0.5M HCl solution in diethyl ether to give the title compound (0.28 g, 47%) as a colorless solid.

後処理

  1. stirringthe resulting mixture was stirred at 30° C. for 24 h
  2. extractionthe mixture was extracted with ethyl acetate (2×10 ml)
  3. washThe organic phase was washed with water (10 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationit was filtered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (petroleum ether-ethyl acetate, 10:1)

出典と根拠

ORDレコード
ord-05014b9f1c45445d9de7fd56b50d8d96
出典データセット
uspto-grants-2009_10
特許番号
US07598384B2

反応ノート

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