Ammonium formate → 3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)aniline

Participants

Reaction Conditions

Reaction Steps

1-(2-Fluoro-4-nitro-phenyl)-4-methyl-1H-imidazole (4.66 g, 21.1 mmol) was dissolved in a mixture of methanol (25 mL) and tetrahydrofuran (100 mL). The solution was cooled to 0° C. under an atmosphere of nitrogen. Ammonium formate (6.64 g, 105 mmol) and 10% palladium on charcoal (0.24 g) was added and the mixture was stirred at 20° C. for 18 h. The mixture was filtered through celite and the celite was washed with methanol. The filtrate was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and 10% aqueous sodium bicarbonate solution. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure to yield the title compound (3.89 g, 97%) as a yellow solid.

Provenance & Evidence