Acetic Acid → HCID 22388007, compound

Participants

Reaction Steps

Methyl 3-(2-chloro-4-nitrobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (705 mg) was suspended in ethanol (6 ml) and reduced iron (655 mg) and acetic acid (2.11 ml) were added, which was followed by refluxing under heating for 3 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate solution to make the residue alkaline and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure to give methyl 3-(4-amino-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (608 mg) as a white powder.

Provenance & Evidence