Pyridine → 9-bromo-3-methylbenzo[f]quinazolin-1(2H)-one

Participants

Reaction Steps

A mixture of 9-Bromo-5,6-dihydro-3-methylbenzo[f]quinazolin-1(2H)-one (1.0 g, 3.4 mmoles), N-bromosuccinimide (0.63 g, 3.5 mmoles) and pyridine (0.3 ml, 3.7 mmoles) in dry benzene (350 ml) was reacted in the same manner as for the corresponding 3-pivalamide (Example 2). After cooling, benzene and excess pyridine were removed under reduced pressure. The residue was triturated with methanol:water (1:1) and filtered to leave a crude product which was recrystallized from methanol to give 9-bromo-3-methylbenzo[f]quinazolin-1(2H)-one as an off-white solid. (0.47 g, 37%) 1H NMR (DMSO-d6, 200 MHz) δ: 2.57 (s, 3H, CH3); 7.73 (d, J=9.0 Hz, 1H, Ar); 7.86 (dd, J=8.6, 2.0 Hz, 1H, Ar); 8.09 (d, J=8.7 Hz, 1H, Ar); 8.41 (d, J=8.8 Hz, 1H, Ar); 9.92 (d, J=2.0 Hz, 1H, Ar).

Provenance & Evidence