Pyridine → N-(3-fluorophenyl)-2-(4-nitro-1H-pyrazol-1-yl)acetamide

Participants

Reaction Steps

A solution of phosphorus oxychloride (668 mg, 4.40 mmol) in tetrahydrofuran (4 ml) was added to a mixture of (4-nitro-1H-pyrazol-1-yl)acetic acid (684 mg, 4.00 mmol), 3-fluoroaniline (500 mg, 4.5 mmol) and pyridine (1.26 g, 16 mmol) in tetrahydrofuran (20 ml) at 0° C. under argon. The resulting mixture was stirred for 1 hour and an aqueous solution of sodium bicarbonate (20 ml) added. The mixture was further diluted with water and extracted with ethyl acetate (3×50 ml). The organic phase was recovered, dried and concentrated to give an oil which was triturated with diethyl ether:petroleum ether (1:1) to yield N-(3-fluorophenyl)-2-(4-nitro-1H-pyrazol-1-yl)acetamide (695 mg, 65% yield):

Provenance & Evidence