Sulfuric Acid → 6-Tert-butyl-2-methylnicotinonitrile

Participants

Reaction Steps

The title compound was synthesized according to the procedure described for the synthesis of 6-tert-butylnicotinonitrile starting from 2-methyl-nicotinonitrile (intermediate 30) (216 mg, 1.7 mmol), pivalic acid (868 mg, 8.5 mmol), AgNO3 (38.5 mg, 0.23 mmol), (NH4)2S2O8 (504 mg, 2.2 mmol) and 3.75 ml 10% H2SO4. Purification by normal phase chromatography with 100% heptane to 90/10 Heptane/EA yielded 240 mg of a mixture of both mono and di-t-butylated pyridines. Material used crude in the preparatin of [1-(6-tert-butyl-2-methylpyridin-3-yl)ethyl]amine (intermediate 32) below.

Provenance & Evidence