Water → 6-Bromo-1,8-naphthyridin-2(1H)-one

Participants

Reaction Steps

A solution of (E)-tert-butyl 3-(2-amino-5-bromopyridin-3-yl)acrylate (2.5 g, 8.35 mmol) in anhydrous methanol (50 mL) was treated with sodium methoxide (8.5 mL of a 4.9 M solution, 41.75 mmol). The solution was heated at reflux for 2 h then cooled to room temperature. The mixture was cooled in an ice-H2O bath and treated with H2O (100 mL) under rapid stirring to give a precipitate. The solid was filtered and washed with H2O (20 mL). The filtrate was neutralized with 1 M HCl(aq) to form a precipitate. The solid was filtered and washed with H2O (20 mL). The solids were combined and dried under reduced pressure to give an off-white solid (1.75 g, 93%). 1H NMR (300 MHz, DMSO-d6) δ 8.43 (d, 1H, J=2.5 Hz), 8.06 (d, 1H, J=2.5 Hz), 7.60 (d, 1H, J=9.1 Hz), 6.44 (d, 1H, J=9.1 Hz); ESI MS m/z 225 (100%); 227 (100%)[C8H5N2OBr+H]+

Provenance & Evidence