Pyridine → 1H-Inden-1-one, 5-bromo-2,3-dihydro-, O-methyloxime

Participants

Reaction Steps

To a solution of 5-bromoindan-1-one (100 g, 0.47 mol) in ethanol (650 ml) under argon was added methoxylamine hydrochloride (198 g, 2.38 mol) and pyridine (125 ml). The mixture was heated under reflux for 2.5 hours, cooled to room temperature and poured into saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate and the organic phase dried and concentrated in vacuo. The crude material was recrystallised from isopropanol to afford the title compound (110 g, 97%); 1H NMR (CDCl3) 7.52 (1H, d, J 8.3 Hz), 7.43 (1H, d, J 1 Hz), 7.35 (1H, dd, J 8.3, 1 Hz), 3.97 (3H, s), 2.99 (2H, m), 2.85 (2H, m).

Provenance & Evidence