Dimethylformamide → HCID 18959435, compound

Participants

Reaction Steps

To dimethylformamide (1.5 ml) solution of diethyl malonate (47.8 μl), was added sodium hydride (24.4 mg) with stirring under ice-cooling, and the mixture was stirred for 20 minutes with ice-cooling. To the solution was added ethyl 1-[N-(chloromethyl)-N-methylamino]-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (100 mg) with stirring under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. The reaction solution was added to a mixed solution comprising ethyl acetate (30 ml) and water (30 ml) for extraction. The organic layer was washed with water (30 ml×3) and a saturated brine(30 ml×3), dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to column chromatography with silica gel (3 g), eluted with a mixed solvent of dichloromethane ethyl acetate (20/1 to 10/1) and concentrated to dryness under reduced pressure to obtain ethyl 6,7,8-trifluoro-1-[N-methyl-N-{2,2-bis(ethoxycarbonyl)ethyl}amino]-1,4-dihydro-4-oxoquinoline-3-carboxylate (49.1 mg).

Provenance & Evidence