Ammonium Chloride → 2-Chloro-6-methylpyridin-4-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-6-methyl-4-nitropyridine 1-oxide (52 g, 0.27 mol) in EtOH and H2O was treated with powdered iron (46 g, 0.83 mol) and NH4Cl (44 g, 0.83 mol). The mixture was stirred at 90° C. for 3 h. After cooling to room temperature the reaction mixture was filtered, and the filtrate was extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with brine (500 mL), dried over magnesium sulfate, filtered and concentrated to afford 2-chloro-6-methylpyridin-4-amine. 1H NMR (400 MHz, CDCl3) δ 6.36 (d, J=1.5 Hz, 1H), 6.28 (d, J=1.2 Hz, 1H), 4.30 (m, 2H), 2.34 (s, 3H). LRMS calc'd for (C6H7ClN2) [M+H]+, 143; found 143.

Provenance & Evidence