Cyanoacetic acid → HCID 70873979, compound

Participants

Reaction Steps

To a stirred mixture of commercially available cyanoacetic acid (1.1 eq, 0.118 g, 1.39 mmole) in dichloromethane was added oxalylchloride (0.353 g, 2.78 mmole, 0.236 mL) and 2 drops N,N′-dimethylformamide). The reaction was stirred for 2 hours at RT until homogenous solution developed. 2-(2-Ethoxy-ethylamino)-benzoic acid ethyl ester (1 eq, 0.300 g, 1.26 mmole) was added and the resulting solution was allowed to stir at RT overnight. Reaction mixture was diluted with saturated sodium bicarbonate water (20 mL) and extracted with ethyl acetate (25 mL×3). Combined organic phase was washed consecutively With water, brine before drying over sodium sulfate. Organic phase was evaporated and the residue was purified by flash chromatography to afford 2-[(2-Cyano-acetyl)-(2-ethoxy-ethyl)-amino]-benzoic acid ethyl ester as clear liquid (0.292 g, 76%, LCMS calc M+H 305, obs M+H 305).

Provenance & Evidence