Hydrochloric Acid → 2-[(1H-Imidazol-2-yl)methyl]aniline

Participants

Reaction Steps

50% Aqueous ethanol (5,672 ml) and 2,890 g (14.22 moles) of 2-(2-nitrobenzyl)imidazole were charged into a 22 liter flask. The suspension was stirred under nitrogen atmosphere and 2,400 g (42.97 moles) of iron powder (100 mesh) were added all at once. The mixture was then warmed to 70° and a solution of 1.7 ml of 12N hydrochloric acid in 8.3 ml absolute ethanol were added. A vigorous exotherm resulted and a strong reflux occurred that persisted for 1.5 hours. When the exotherm subsided, a mixture of 290 ml of 12N HCl and 1400 ml of absolute ethanol were added over 30 minutes. Heat was applied and the mixture was refluxed for 2 hours, diluted with 6,500 ml of absolute ethanol and adjusted to pH 8-9 with 700 ml of 10N sodium hydroxide. The suspension was stirred for 1 hour and filtered. The cake was washed with 1,000 ml of absolute ethanol, the filtrates were combined and the solvent was removed. The remaining solid was then suspended in 10,000 ml of water, stirred under nitrogen atmosphere for two hours, collected, washed with 2,000 ml of water, and dried to yield 2-(2-aminobenzyl)imidazole, m.p. 153°-155°.

Provenance & Evidence