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

HRID 1817820노트

반응식

HRID 1817820 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a1777af844ac401cb7e3ca7d9dce4982
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598384B2

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