N-bromobutanimide → HCID 66882576, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (6-chloro-3-methyl-quinolin-5-yl)-acetic acid methyl ester (1.70 g, 6.81 mmol) in tetrachloromethane (140 mL) was added N-bromosuccinimide (1.28 g, 6.8 mmol). The reaction mixture was heated to 40° C. for 1 h under simultaneous irradiation by a 300 W UV lamp. The reaction mixture was filtered and the filtrate concentrated in vacuo. The crude product was purified by flash column chromatography (silica gel, gradient of cyclohexane/EtOAc 100:0 to 80:20) to afford the title compound as a white powder (1.34 g, 4.1 mmol, 60%). %). 1H NMR (400 MHz, CDCl3, 298 K): δ=8.97 (s, 1H), 8.30 (s, 1H), 8.07 (d, J=9.0 Hz, 1H), 7.76 (d, J=9.0 Hz, 1H), 4.69 (s, 2H), 4.30 (s, 2H), 3.73 (s, 3H). MS (ES+): 328 (M(Cl3H1179Br35ClNO2)+H)+.

Provenance & Evidence