Ammonium Chloride → 2-methyl-6-(1H-1,2,4-triazol-1-yl)pyridin-3-amine

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A mixture of zinc (Aldrich, <10 micron; 798 mg, 12.2 mmol) in aqueous ammonium chloride (2 M; 6.1 mL, 12.2 mmol) was cooled to 0° C. using an ice-water bath, and stirred at this temperature for 15 min. A solution of 2-methyl-3-nitro-6-[1,2,4]triazol-1-yl-pyridine (500 mg, 2.44 mmol) in ethyl acetate (8 mL) was added and the mixture was stirred at 0° C. for 1 h and then at room temperature overnight. The mixture was then filtered through Celite™ to remove zinc dust, and the Celite™ was washed with ethyl acetate and methanol. Water and ethyl acetate were added to the filtrate and the mixture was shaken and then filtered to remove some solid material between the two layers. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers were evaporated to dryness under high vacuum to give 2-methyl-6-[1,2,4]triazol-1-yl-pyridin-3-ylamine (322 mg, 75%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 2.30 (s, 3H), 5.37 (s, 2H), 7.11 (d, 1H, J=8.4 Hz), 7.38 (d, 1H, J=8.4 Hz), 8.13 (s, 1H), 9.03 (s, 1H).

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