1-(3-fluoro-4-nitrophenyl)-1H-1,2,4-triazole → 2-Fluoro-4-(1,2,4-triazol-1-yl)phenylamine

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Reaction Steps

1-(3-Fluoro-4-nitrophenyl)-1H-1,2,4-triazole (3.06 g) was dissolved in ethanol (100 ml) and admixed with 10% Pd/C (50% water, 612 mg) and then stirred under a hydrogen atmosphere at room temperature for 1 hour. After filtering the catalyst off, the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate, and the resultant solution as washed successively with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1:2). A desired fraction was concentrated under reduced pressure and the residue was crystallized from a mixture of ethyl acetate and diisopropyl ether to yield 1-(4-amino-3-fluorophenyl)-1H-1,2,4-triazole (1.68 g) as yellow powdery crystals.

Provenance & Evidence