Ammonium Chloride → 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone oxime (320 mg, 1.08 mmol), zinc (3.53 g, 54.00 mmol), and ammonium chloride (2.89 g, 54.00 mmol) in MeOH (10 mL) and HOAc (2 mL) was heated at 60° C. for 4 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. To the residue was added an aqueous solution of ammonia (50 mL) and the resulting mixture was extracted with DCM (50 mL×3). The combined extracts were dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with CH2Cl2:MeOH:Et3N (10:1:0.2) to afford 200 mg (66%) of 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanamine as a colorless oil. MS (ESI): m/z=283.2[M+1]+.

Provenance & Evidence