Benzylamine → 2-Benzylamino-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one hydrochloride

HRID 1817820ノート

反応式

HRID 1817820 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][C:6]([CH3:14])([CH3:13])[CH2:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[H-].[Na+]>C(#N)C.O.CS(C)=O>[ClH:1].[CH2:21]([NH:28][C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][C:6]([CH3:14])([CH3:13])[CH2:5][C:4]=2[N:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

8

反応物 4

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 148125452-Chloro-7,7-dimethyl-7,8-dihydroquinolin-5(6H)-one

生成物 1

HCID 690384072-Benzylamino-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one hydrochloride収率 21%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

2-Chloro-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one (0.315 g, 1.5 mmol) and potassium carbonate (0.83 g, 6 mmol) were added to a solution of benzylamine (0.2 g, 1.8 mmol) in dry acetonitrile (4 ml). The mixture was stirred at reflux for 48 h. DMSO (3 ml) and sodium hydride (0.05 g) were added and heating was continued for additional 5 h. Water (10 ml) was added and the mixture was extracted with chloroform (2×10 ml). The extract was dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (chloroform-methyl alcohol, 40:1), then treated by dry HCl in diethyl ether to give the title compound (0.1 g, 21%) as a colorless solid.

後処理

  1. temperatureat reflux for 48 h
  2. temperatureheating
  3. extractionthe mixture was extracted with chloroform (2×10 ml)
  4. dry with materialThe extract was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (chloroform-methyl alcohol, 40:1)
  8. additiontreated by dry HCl in diethyl ether

出典と根拠

ORDレコード
ord-a1777af844ac401cb7e3ca7d9dce4982
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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