1-(3-nitrophenyl)-1H-imidazole → 3-(1H-imidazol-1-yl)aniline

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Reaction Steps

A solution of 1-(3-nitrophenyl)-1H-imidazole (6.5 g, 34 mmol) in glacial acetic acid (50 ml) was treated with 10% palladium on charcoal (320 mg) and hydrogenated at 50 psi until hydrogen uptake ceased (ca. 3 hours). The mixture was filtered through a glass microfibre filter paper (Whatman GF/A) and evaporated to dryness. The residue was azeotroped twice with toluene to give 3-(imidazol-1-yl)phenylamine as a yellow oil (5.5 g, 100%) which was used without purification. m/z (ES+) 360 (M++H).

Provenance & Evidence