Sodium Methoxide → 5-Bromo-2-methoxyquinoline

Participants

Reaction Steps

To a suspension of 5-bromo-2-chloroquinoline (2.81 g, 11.6 mmol) in MeOH (25 mL) was added sodium methoxide (30% w/w in MeOH, 10.4 mL, 54.7 mmol). The mixture was refluxed for 3 hours, allowed to cool to room temperature, diluted with water, then extracted with EtOAc. The combined extracts were washed with water then saturated NaCl (aq), dried over Na2SO4, filtered, then concentrated to afford the title compound as a white solid: 1H NMR (500 MHz, CDCl3): δ 8.36 (d, J=9.1 Hz, 1H); 7.81 (d, J=8.4 Hz, 1H); 7.63 (dd, J=7.6, 1.1 Hz, 1H); 7.46 (t, 1H, J=7.9 Hz); 6.98 (d, J=9.1 Hz, 1H); 4.08 (s, 3H); LC1 1.85 min. (M+H) 238.

Provenance & Evidence