Dichloromethane → 3-Cyanomethyl-1-(4-fluorophenyl)-pyrrolidine-2,5-dione

Participants

Reaction Conditions

Reaction Steps

A mixture was prepared of 48.3 g (0.2 moles) 3-chloromethyl-1-(4-fluorophenyl)-pyrrolidine-2,5-dione (according to Example 1), 300 ml methylene chloride and 7 g hexadecyltrimethylammonium chloride, dissolved in 80 ml water. To this mixture, a solution of 28.6 g (0.43 moles) potassium cyanide in 90 ml water was added dropwise at 0° C., and then stirred for 4 hours at 0° C. and another 12 hours at 20° C. The resulting phases were then separated with the organic phase being washed with water and dried with sodium sulfate. Finally, methylene chloride was distilled off and the residue dissolved in 250 ml toluene. Upon standing, the desired product crystallized. The actual yield was 44.1% of the theoretical yield. Melting point 97° C.

Provenance & Evidence