Hydrochloric Acid → Ethyl 2-cyano-2-(hydroxyimino)acetate

Participants

Reaction Conditions

Reaction Steps

A solution of sodium nitrite (57.30 g, 830.60 mmol) in water (710.00 ml) was treated with ethyl cyanoacetate (100.00 g, 884.00 mmol). 85% Orthophosphoric acid (36.60 ml, 540.00 mmol) was added dropwise over 45 min, while keeping the temperature of the reaction mixture below 35° C. with the aid of an ice bath. At the end of the addition, the mixture was warmed to 40° C. and stirred for 1 hour. The reaction was quenched at 45° C. with fuming HCl (73.90 ml, 880.00 mmol), and the mixture was then left to cool to room temperature and at 0° C. overnight to complete precipitation. The solid was filtered, the filtrate washed with water and dried under high vacuum overnight to yield 70 g of cyano-hydroxyimino-acetic acid ethyl ester as white crystals. A second batch was obtained by extracting the mother liquor with ether (44.00 g, total yield 91%).

Provenance & Evidence