Acetic Acid → 2-[5-(Diethoxymethyl)-1-methyl-1H-1,2,4-triazol-3-yl]-6-methylpyridine

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Reaction Steps

Methyl 2,2-diethoxyethanimidoate (42 g, 0.26 mol) was dissolved in methanol (200 mL), and a solution of compound N′,6-dimethylpyridine-2-carbohydrazonamide (43 g, 0.25 mol) in methanol (200 mL) while cooling with a water bath, followed by the addition of acetic acid (22 mL, 0.37 mol). The mixture was stirred at room temperature for 3 h, and then K2CO3 (10 g, 0.071 mol) was added. The mixture was stirred for 10 min, and then the methanol was evaporated. The residue was stirred with a solution of K2CO3 (20 g) in water (200 mL), and extracted with ether (2×150 mL). The organic layer was washed with water and then saturated NaCl solution, dried over Na2SO4 and evaporated. The residue (62 g) was purified by chromatography on a silica gel column to afford 39.5 g (57%) of the title product.

Provenance & Evidence