Hydrochloric Acid → N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Participants

Reaction Steps

A mixture of N-[6-(3-nitrophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (3.84 g, 11.3 mmol), zinc (5.17 g, 79.1 mmol), hydroxylammonium chloride (3.02 g, 56.5 mmol) and methanol (30 mL) was stirred under refluxing conditions for 3 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethanol (50 mL), and reduced iron (5.00 g, 89.5 mmol), concentrated hydrochloric acid (5 mL) and water (50 mL) were added. The mixture was stirred under refluxing conditions for 1 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was collected by filtration and washed with ethyl acetate to give the title compound (862 mg, 25%) as a white solid.

Provenance & Evidence