Sodium Bicarbonate → (7-Fluoro-2-methoxy-quinolin-8-yl)-methanol

Participants

Reaction Steps

A suspension of 8-bromomethyl-7-fluoro-2-methoxy-quinoline (25 g, 92.56 mmol) in acetone (360 mL) and water (460 mL) was treated with NaHCO3 (12.74 g, 151.64 mmol, 1.6 eq). The mixture was heated to reflux overnight. After cooling, the volatiles were removed in vacuo and the residue was partitioned between EA (300 mL) and water (100 mL). The aq. layer was extracted once with EA (250 mL) and the combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by CC (Hept-EA 3:1) to afford the title alcohol as a yellowish solid (14.04 g).

Provenance & Evidence