Dimethylformamide → HCID 23359082, compound
Reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:14]([OH:16])=[O:15])[CH:6]=[C:7]2C=1NC(=O)[CH2:9][CH2:8]2)[CH3:2].[H-].[Na+].[CH3:19]I.[CH3:21][N:22]([CH3:25])[CH:23]=[O:24]>>[CH3:21][N:22]1[C:25]2[C:7](=[CH:6][C:5]([C:14]([O:16][CH3:19])=[O:15])=[CH:4][C:3]=2[CH2:1][CH3:2])[CH2:8][CH2:9][C:23]1=[O:24]Participants
Procedure
10 g of 8-ethyl-6-carboxy-3,4-dihydrocarbostyril was gradually added to a solution of 4.2 g of sodium hydride in 50 ml of dimethylformamide with ice-cooling. The mixture was stirred at room temperature for 30 minutes. Thereto was dropwise added a solution of 9.0 ml of methyl iodide in 20 ml of dimethylformamide with ice-cooling. The mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water. The resulting mixture was extracted with methylene chloride. The extract was washed with water and a saturated aqueous sodium chloride solution in this order, then dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (elutant: methylene chloride/methanol=100/0 to 100/5) to obtain 10.0 g of 1-methyl-8-ethyl-6-methoxycarbonyl-3,4-dihydrocarbostyril as a colorless oil.
Workup
- temperaturecooling
- temperaturecooling
- stirringThe mixture was stirred at room temperature overnight
- extractionThe resulting mixture was extracted with methylene chloride
- washThe extract was washed with water
- dry with materiala saturated aqueous sodium chloride solution in this order, then dried with anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto remove the solvent
- customThe residue was purified by silica gel column chromatography (elutant: methylene chloride/methanol=100/0 to 100/5)
Sources & evidence
- ORD record
- ord-a6a3981f1fe9497790aec2b03e904547
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05591751
Reaction notes
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