2,6-Dichloro-3-nitropyridine → 6-Chloro-3-nitropyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dichloro-3-nitropyridine (40 g, 207 mmol) and CuCN (22.32 g, 248 mmol) in 1-methyl-2-pyrrolidinone (160 ml) was quickly heated to 180° C. for 25 minutes. The mixture was cooled to room temperature and the deep brown solution was poured into ice water (1200 ml) and stirred for 30 min. The aqueous solution was extracted with ethyl acetate and boiling toluene, the organic layer was dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (5% to 25% Ethyl Acetate gradient in Pentane) to give 6-chloro-3-nitropicolinonitrile as a yellow solid. (15.75 g, 41.4% yield)

Provenance & Evidence