Sodium Cyanide → 5-Methylpicolinonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-fluoro-5-methylpyridine (39 g; 351.5 mmol) in 141 ml of dimethylsulfoxide was added 17.23 g of sodium cyanide (351.5 mmol). After stirring for 3 days at 150° C., an additional 3 g of sodium cyanide was added and heating was continued for 5 hours. The reaction mixture was cooled to 25° C. then poured into 525 ml of ice water. The solution was filtered through a coarse fritted funnel and a dark brown solid was collected. The solid was air dried to give 17 g of the desired cyanopyridine: Anal Calc'd. for C7H6N2: C, 71.17; H, 5.12; N, 23.71. Found: C, 69.91; H, 5.24; N, 23.26.

Provenance & Evidence