Dimethylformamide → HCID 57476000, compound

Participants

Reaction Steps

A mixture of ethyl 4-methyl-7-nitro-1H-indole-2-carboxylate (7.0 g), 60% sodium hydride (1.35 g) and N,N-dimethylformamide (40 mL) was stirred at room temperature for 30 min. The solution was ice-cooled, and a solution (15 mL) of chloromethyl methyl ether (2.6 mL) in tetrahydrofuran was added dropwise. The mixture was stirred at 4° C. for 4 hr, and the reaction solution was diluted with ethyl acetate, washed with aqueous citric acid solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=5:95-1:5) to give the title compound (5.6 g, yield 68%) as pale-yellow needle crystals.

Provenance & Evidence