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

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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 formiate (6.64 g, 105 mmol) and 10% palladium on charcoal (0.24 g) were added and the mixture was stirred at ambient temperature for 18 hours. It was filtered through celite. The celite was washed with methanol and the filtrate was evaporated under reduced pressure to dryness. 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 the solvent was evaporated under reduced pressure to yield the title compound (3.89 g, 97%) as a yellow solid. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=7.62 (s, 1H), 7.12 (t, 1H), 7.01 (s, 1H), 6.41-6.51 (m, 2H), 5.64 (br s, 2H), 2.13 (s, 3H).

Provenance & Evidence