O-Methylhydroxylamine hydrochloride → HCID 53895774, compound

Participants

Reaction Steps

Potassium t-butoxide (0.11 g, 1.0 mmole) was added to methanol (10 ml) with stirring under argon and after 20 minutes at room temp. the solution was treated with methoxylamine hydrochloride (0.11 g, 1.3 mmole). The resulting mixture was stirred at room temp. for 20 minutes, then treated with a solution of 1-(4'-acetyl-2'-methylbiphenyl-4-carbonyl)-6-(2-dimethylaminoethoxy)-5-methoxy-1H-indole (E5, 0.30 g, 0.63 mmole) in methanol (10 ml). The mixture was stirred for 18 h at room temp. followed by heating under reflux for 3 h, then concentrated in vacuo. The residue was treated with 10% Na2 CO3 solution and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to leave a yellow oil, which was chromatographed on silica gel eluting with 0-5% methanol/dichloromethane to afford the title compound (0.20 g, 63%), mp 120°-121° C.

Provenance & Evidence