Dimethylformamide → 5-Methylpicolinonitrile

Participants

Reaction Steps

2-Bromo-5-methylpyridine ((8.6 g, 50 mmol) was mixed with Zn(CN)2 (4.1 g, 35 mmol), Pd(dppf)2C12 (0.89 g, mmol) and zinc dust (0.14 g, mmol) in DMF (86 ml) at 155° C. for 15 minutes. The reaction mixture was cooled down to room temperature and quenched with water and ethyl acetate. The mixture was filtered through celite and the organic layer was separated and dried with sodium sulfate. The product was purified by column chromatography with 10˜25% ethyl acetate in hexanes to give 3.4 g of 5-methyl-pyridine-2-carbonitrile (yield: 57.6%). 1H NMR (CDCl3), δ(ppm): 8.52 (s, 1H), 7.59 (m, 2H), 2.42 (s, 1H).

Provenance & Evidence