Sodium Hydroxide → 5-Bromo-1-oxo-1lambda~5~-quinoline

Participants

Reaction Steps

To a solution of 5-bromoquinoline (2.5 g, 12.02 mmol) in DCM (50 mL) was added m-CPBA (3.50 g, 15.62 mmol) in three portions at room temperature. Upon completion of addition, the reaction mixture was stirred at room temperature for 3 h. After this time, 1N NaOH (40 ml) was added to the reaction, and the resulting mixture was extracted with DCM (2×50 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to afford the title compound (2.7 g, 99% yield) as light yellow solid. LCMS, [M+H]+=223.9. 1H NMR (400 MHz, CDCl3) δ 8.75 (d, J=8.8 Hz, 1H), 8.65 (d, J=6.0 Hz, 1H), 8.18 (d, J=8.8 Hz, 1H), 7.95 (d, J=7.7 Hz, 1H), 7.68-7.56 (m, 1H), 7.44 (dd, J=8.2, 6.0 Hz, 1H).

Provenance & Evidence