Hydrochloric Acid → 1-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole

Participants

Reaction Steps

A solution of 2-chloro-5-nitroanisole (1.0 g, 5.2 mmol), 3-methyl-1H-1,2,4-triazole (1.74 g, 20.9 mmol) and potassium hydroxide (0.44 g, 7.8 mmol) in dimethyl sulfoxide (5 ML) was heated to 80° C. under an atmosphere of nitrogen for two days. Water and 1M aqueous hydrogen chloride solution was added and the reaction was stirred for 45 minutes. The precipitate was filtered off, washed with water, dissolved in dichloromethane. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed with water, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by reversed preparative HPLC using acetonitril/water (0.1% formic acid) to yield the title compound as a yellow solid (77 mg, 6%). MS ISP (m/e): 235.2 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.88 (s, 1H), 8.10 (d, 1H), 7.96-8.02 (m, 2H), 4.10 (s, 3H), 2.51 (s, 3H).

Provenance & Evidence