Pivalic acid → 6-Tert-butyl-2-chloropyridine-3-carbonitrile

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Reaction Steps

The title compound was synthesized according to the procedure described for the synthesis of 6-tert-butylnicotinonitrile starting from 2-chloronicotinonitrile (3.91 g, 28 mmol), pivalic acid (14.4 g, 141 mmol), AgNO3 (0.622 g, 3.66 mmol), (NH4)2S2O8 (8.36 g, 36.6 mmol) and 50 ml 10% H2SO4. Purified by normal phase chromatography using 100 heptane to 95/5 heptane/ethyl acetate. (Yield: 42%, 2.3 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.34 (s, 9 H), 7.36 (d, J=8.20 Hz, 1 H), 7.88 (d, J=8.20 Hz, 1 H).

Provenance & Evidence