3-Cyanopyridine → 6-Tert-butylpyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-cyanopyridine (10 g, 96 mmol), trimethylacetic acid (9.8 g, 96 mmol) and silver nitrate (1.63 g, 9.6 mmol) in 10% aqueous sulfuric acid (100 ml) at 70° C. was added dropwise a solution of ammonium peroxodisulfate (21.9 g, 96 mmol) in water (120 ml). After complete addition the mixture was stirred at 70° C. for 2 hours. The mixture was cooled and basified by the addition of 33% aqueous NH4OH, and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine (100 ml), dried (Na2SO4) and evaporated to give the title compound (15.6 g, 100%).

Provenance & Evidence