Ammonium Chloride → N-(6-aminopyridin-3-yl)methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-(6-nitro-pyridin-3-yl)-methanesulfonamide (298 mg, 1.37 mmol) in methanol (8.3 mL) was treated with a solution of ammonium chloride (154 mg, 2.88 mmol) in water (1 mL). This solution was stirred at 25° C. for 5 min. At this time, zinc dust (879 mg, 13.44 mmol) was added to the reaction. The resulting reaction mixture was then heated under reflux for 3 h. At this time, the reaction was cooled to 25° C. and then was filtered through a pad of celite (9/1 methylene chloride/methanol wash). The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 9/1 methylene chloride/methanol) afforded N-(6-amino-pyridin-3-yl)-methanesulfonamide (196.3 mg, 76.4%) as a reddish-brown oil: EI-HRMS m/e calcd for C6H9N3O2S (M+) 184.0415, found 184.0415.

Provenance & Evidence