1-(4-nitrophenethyl)-1H-imidazole → 4-[2-(1H-imidazol-1-yl)ethyl]aniline

Participants

Reaction Steps

A solution of 10 g (0.046 mole) of 1-[2-(4-nitrophenyl)ethyl]-1H-imidazole in 100 mL of ethanol, 50 mL of 10% aqueous hydrochloric acid and 1.0 g of 5% Pd/C catalyst are placed in a small Parr bottle and hydrogenated at 50 psi pressure for about 24 hours. Additional H2 is added as needed to maintain 50 psi pressure. The reaction mixture is filtered and the solvent is concentrated in vacuo. The residue is dissolved in 100 mL of water and made basic (pH 9) with potassium carbonate. Extract the aqueous mixture with methylene chloride (2×100 mL) and combine. Evaporation of the solvent yields the title compound.

Provenance & Evidence