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

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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-methoxynicotinonitrile (8.02 g, 5.98 mmol), pivalic acid (3.05 g, 39.9 mmol), AgNO3 (0.13 g, 0.78 mmol), (NH4)2S2O8 (1.78 g, 7.78 mmol) and 6 ml 10% H2SO4. Purified by normal phase chromatography using 95/5 to 90/10 heptane/ethyl acetate. (Yield: 80 mg, 7%). 1H NMR (400 MHz, CDCl3) δ ppm 1.33 (s, 9 H), 4.04 (s, 3 H), 6.97 (d, J=7.81 Hz, 2 H), 7.78 (d, J=7.81 Hz, 2 H).

Provenance & Evidence