2-Amino-4-methylpyridine → 2,2-Dimethyl-N-(4-Methyl-2-pyridyl)propionamide

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Reaction Steps

To a solution of 4-methylpyridin-2-amine (25.0 g, 0.230 mol) and Et3N (35.0 g, 0.350 mmol) in CH2Cl2 (200 ml) was added pivaloyl chloride (33.1 g, 0.270 mol) drop-wise. The mixture was stirred for 4 h under N2 atmosphere. The reaction mixture was quenched with water and was extracted with ethyl acetate (200 mL×3). The combined organic extracts were dried over anhydrous Na2SO4, evaporated under vacuum and purified by chromatography on silica gel (20% ethyl acetate in petroleum ether) to afford N-(4-methylpyridin-2-yl)pivalamide (36.2 g, 82%). 1H NMR (CDCl3, 300 MHz) δ 8.08-8.09 (m, 2H), 8.00 (br s, 1H), 6.83 (dd, J=4.8, 0.6 Hz, 1H), 2.33 (s, 3H), 1.30 (s, 9H).

Provenance & Evidence