Ammonium formate → HCID 22933920, compound

Participants

Reaction Steps

To a solution of 6-chloro-2-fluoro-3-methyl-4-nitrophenol (4.11 g, 19.9 mmol) in ethanol (200 ml) were added 10%-palladium/carbon (containing 50% water, 410 mg) and ammonium formate (15.1 g, 240 mmol), and the resulting mixture was stirred for 3 hours with heating under reflux while maintaining the temperature. The mixture was filtered by the use of Celite and the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was partitioned by the use of water and ethyl acetate (the aqueous layer was adjusted to pH 6 to 7 with a 5% aqueous sodium hydrogencarbonate solution and re-extracted), and the organic phase was washed with a 5% aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to obtain 4-amino-2-fluoro-3-methylphenol (2.89 g, 100%).

Provenance & Evidence