Dimethylformamide → 5-Chloro-2-cyanopyridine

Participants

Reaction Steps

The compound (10.0g) obtained in (1) above, dimethylformamide (50 ml), copper cyanide (6.98 g), triethylamine (10.9 ml) and molecular sieves 4A (2 g, heat-treated) were placed in an autoclave. The outer temperature was set for 200° C. and the mixture was stirred for 4 hours. Water and ethyl acetate were added to the reaction mixture, and, after filtering off insoluble matters, extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel column chromatography (hexane-ethyl acetate) to give 1.92 g of a white solid (yield 27%).

Provenance & Evidence