N-bromobutanimide → 9-bromomethyl-3-methylbenzo[f]quinazolin-1(2H)-one

Participants

Reaction Steps

To a hot solution of 3,9-dimethylbenzo[f]quinazolin-1(2H)-one (4.00 g, 17.9 mmol) in benzene (2000 ml) under nitrogen was added N-bromo-succinimide (4.00 g, 22.5 mmol). The reaction mixture was stirred just below reflux for 30 minutes, then at a gentle reflux for 30 minutes. The resulting suspension was allowed to cool for 2 hours, the solid filtered and dried at 70° C. under reduced pressure to give 9-bromomethyl-3-methylbenzo[f]quinazolin-1(2H)-one (4.32 g, 83% purity by NMR). 1H NMR (DMSO-d6, 300 MHz) δ: 2.45 (s, 3H, CH3, 4.96 (s, 2H, CH2), 7.65 (d, J=9 Hz, 1H, Ar), 7.70 (dd, J=8,2 Hz, 1H, Ar), 8.05 (d, J=8 Hz, 1H, Ar), 8.16 (d, J=9 Hz, 1H, Ar), 9.89 (s, 1H, Ar), 12.7 (br s, 1H, NH).

Provenance & Evidence