Formic Acid → N-[(5-Fluoro-2-pyridinyl)methyl]formamide

Participants

Reaction Steps

In a round-bottomed flask, (5-fluoro-pyridin-2-yl)methylamine (557 mg, 4.42 mmol) was dissolved in 88% formic acid (3.6 ml, 82.6 mmol). The brown solution was stirred at reflux in an oil bath overnight. The reaction mixture was cooled to 0° C. and adjusted carefully to pH=9 by addition of 25% aqueous ammonium hydroxide. The mixture was diluted with water and the aqueous layer was extracted with dichloromethane (3×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give 614 mg (90%) of N-(5-fluoro-pyridin-2-ylmethyl)-formamide as a brown oil which was used without further purification.

Provenance & Evidence