Potassium Cyanide → HCID 54032708, compound

Participants

Reaction Conditions

Reaction Steps

A cold solution of 3.4 g (49.3 millimoles) of sodium nitrite in 25 ml of water is added to a solution of 10.0 g (48.7 millimoles) of cis-2-(p-aminobenzoyl)-cyclopropanecarboxylic acid (see Example 9a) in 37 ml of concentrated hydrochloric acid and 190 ml of water, whilst stirring at 0° C. The mixture is then stirred for a further 10 minutes, at 0°-5° C., after which it is neutralized with sodium carbonate at the same temperature. The solution obtained is added dropwise, whilst stirring, to a cold (0°-5° C.) solution of 5.3 g (59.2 millimoles) of copper-(I) cyanide and 7.5 g (115.2 millimoles) of potassium cyanide in 150 ml of water, which is covered with a layer of 40 ml of toluene. The mixture is then stirred for 30 minutes at 5° C., followed by 12 hours at room temperature. It is filtered and the filtrate is acidified with concentrated hydrochloric acid. The solid which precipitates is filtered off, washed with water and extracted with hot ethanol. Concentrating the ethanol extract gives 3.5 g (33% of theory) of cis-2-(p-cyanobenzoyl)-cyclopropanecarboxylic acid as pale brown crystals, of melting point 180°-182° C.

Provenance & Evidence