N-bromobutanimide → 6-(Bromomethyl)-1-methylquinolin-2(1H)-one

Participants

Reaction Steps

A stirred solution of 28b (22 g, 0.127 mol) and N-bromosuccinimide (23 g, 0.13 mol) in CCl4 (400 mls) was irradiated for 2.5 hours with a 275 watt heat lamp after an addition of AIBN (50 mg) to initiate the free radical reaction. During this time, the reaction achieved reflux. After cooling, the mixture was concentrated to a small volume and ethyl acetate (400 mls) and water (150 mls) were added and the layers separated. The organic phase was dried (MgSO4) and evaporated. The crude material was purified by chromatography on silica gel using 35% ethyl acetate/toluene to give the product 28c (10.4 g, 33%) as a solid, mp 99°-100° C. The structural assignment was supported by the 1H-NMR spectrum. Analysis calculated for C11H10NOBr: C, 52.41; H, 4.00; N, 5.56; Br, 31.69. Found: C, 52.11; H, 3.91; N, 5.40; Br, 31.40.

Provenance & Evidence