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

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.

1. temperatureat reflux in an oil bath overnight
2. extractionthe aqueous layer was extracted with dichloromethane (3×)
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated

ORD record

ord-dcaa0bd1275549859f05e0b2c3636d5b

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2