Ethyl chloroacetate → HCID 67857985, compound

Participants

Reaction Steps

A solution of N-(1H-pyrrol-1-yl)-4-pyridinamine (5 g) in 25 ml of dimethylformamide was slowly added to a suspension of sodium hydride (60% oil dispersion, 1.4 g, washed with hexane) in 5 ml of dimethylformamide. After the anion formation, the mixture was cooled with an ice-salt bath, and a solution of ethyl chloroacetate (4.2 g) in 5 ml of dimethylformamide was slowly added. After thirty minutes, the mixture was stirred with ice water and extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated to 8 g of oil. This oil was purified by HPLC (silica, ethyl acetate) to give 4.1 g of solid, mp 92°-95°. This material was converted to the hydrochloride salt and recrystallized twice from isopropanol and once from ethanol to give 2.6 g of crystals, d 240°-241°.

Provenance & Evidence