Diethylamine → 3-benzoyl-2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline
Reaction equation
[C:1]([C:9]1[C:10]([CH2:33]Br)=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)=[CH:16][C:15]([O:29][CH3:30])=[C:14]([O:31][CH3:32])[CH:13]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:35]([NH:37][CH2:38][CH3:39])[CH3:36]>ClCCl>[C:1]([C:9]1[C:10]([CH2:33][N:37]([CH2:38][CH3:39])[CH2:35][CH3:36])=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)=[CH:16][C:15]([O:29][CH3:30])=[C:14]([O:31][CH3:32])[CH:13]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
A mixture of 3-benzoyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (1.5 g), diethylamine (1.05 g) and dichloromethane (40 ml) was stirred under reflux for 14 hours. The reaction mixture was washed with water, dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform gave 3-benzoyl-2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (0.97 g, 66%). This compound was recrystallized from ethyl acetate-hexane to give colorless prisms, mp. 150°-151° C.
Workup
- temperatureunder reflux for 14 hours
- washThe reaction mixture was washed with water
- dry with materialdried over magnesium sulfate
- customthe solvent was evaporated
- washThe fractions eluted with chloroform
Sources & evidence
- ORD record
- ord-778856fa9f6347828c994281ebf6e6b5
- Source dataset
- uspto-grants-1997_06
- Patent number
- US05641788
Reaction notes
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