N-methyl-2-pyrrolidone → 6-Chloro-3-nitropyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dichloro-3-nitropyridine and cuprous cyanide in 1-methyl-2-pyrrolidinone was quickly heated to 180° C. and maintained at that temperature for 15 minutes with vigorous stirring. The mixture was cooled to −10° C. and the deep brown solution was poured into ice water (3.5 L) and stirred for 30 min. The flocculent brown precipitate was collected and washed with H2O. After drying for about 1.5 h, the moist solid was extracted with boiling toluene (3×300 mL). The combined toluene extracts were washed with H2O, brine, and dried (MgSO4), concentrated. The crude product was crystallized from EtOAc/hexane to afford the title compound: mp 115-117° C.; 1H NMR(DMSO-d6) δ 8.16 (dd, 1H, J=8.7, 3.0 Hz), 8.82 (d, 1H, J=9.0 Hz); MS (EI) m/z 183/185 (M+H)+; Anal. Calc. For C6H2ClN3O2: C, 39.26, H, 1.10, N, 22.89. Found: C, 39.47, H, 1.38, N, 22.77.

Provenance & Evidence