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

HRID 1817820Notes

Reaction equation

HRID 1817820 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a1777af844ac401cb7e3ca7d9dce4982
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

Loading…