Imidazole → 1-(4-Nitrobenzyl)-1H-imidazole

Participants

Reaction Steps

Potassium carbonate (2.00 g; 14.6 mmol) was added to a stirred solution of 1-(bromomethyl)-4-nitrobenzene (3.20 g; 14.8 mmol) and imidazole (1.00 g; 14.7 mmol) in acetonitrile (60 mL). The mixture was stirred at room temperature for 17 hr and then concentrated under reduced pressure. The residue was partitioned between EA and water and the phases separated. The aqueous phase was extracted twice with EA; and the combined organic layers washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to give 1-(4-nitrobenzyl)-1H-imidazole (1.27 g) as a red/brown oil. A solution of 1-(4-nitrobenzyl)-1H-imidazole (2.67 g; 13.1 mmol) in ethanol (100 mL) was hydrogenated at atmospheric pressure with 10% palladium on carbon (0.285 g) at room temperature for 4.5 hr. The mixture was filtered through diatomaceous earth and then concentrated under reduced pressure to give 4-[(1H-imidazol-1-ylmethyl]benzenamine (2.24 g) as a white solid.

Provenance & Evidence