Acetic Acid → N-[2-Amino-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-3,5-dimethoxy-4-methyl-benzamide

Participants

Reaction Steps

A suspension of compound 1f (2.80 g, 6.81 mmol) in a mixture of ethanol (120 mL), acetic acid (6 mL) and water (24 mL) was heated to reflux. Iron powder (1.90 g, 34 mmol) was added portionwise over 45 min. The reaction mixture was cooled to rt and diluted with ethyl acetate. The ethyl acetate solution was washed with saturated NaHCO3 solution, dried Na2SO4, and concentrated on a rotary evaporator to a volume of ˜30 mL. The solid precipitate was recovered by filtration and washed with ethyl acetate (2×). The filtrate was passed through a short silica gel column in ethyl acetate, and concentrated on a rotary evaporator. The residue was triturated with ethyl acetate and combined with the previously filtered solid to afford compound 1g (1.83 g, 70%) as a tan solid. ESI-MS m/e 383.3 (M+1).

Provenance & Evidence