Chlorosuccinimide → 2-Amino-5-chloro-isonicotinonitrile

Participants

Reaction Conditions

Reaction Steps

2-Amino-4-cyanopyridine (8.00 g, 67.2 mmol) was dissolved in DMF (40 mL), and the solution was stirred at 50° C. for 1 hour after adding N-chlorosuccinimide (8.97 g, 67.2 mmol). After the reaction was completed, a sodium hydrogen carbonate aqueous solution was added under ice-cooled condition, and the precipitated solid was collected by filteration. The resulting solid was purified by silica gel column chromatography (chloroform/methanol=95/5→90/10, heptane/ethyl acetate=65/35→50/50) to give 2-amino-5-chloro-4-cyanopyridine (6.23 g, yield 60%) and 2-amino-3-chloro-4-cyanopyridine (0.254 g, yield 2%).

Provenance & Evidence