6-Methoxy-8-nitroquinoline → 8-Nitroquinolin-6-ol

Participants

Reaction Steps

A solution of 6-methoxy-8-nitro-quinoline (9 g, 44.1 mmol) in HBr (100 mL) as heated at 110° C. overnight. Additional HBr (80 mL) was added and the reaction continued to heat for an additional 24 hours. The cooled reaction mixture was basified with 2.5 N NaOH (800 mL) and extracted into EtOAc (2×300 mL). The organic fractions were combined, dried over Na2SO4 and purified by column chromatography (50% EtOAc/hexane) to afford 2.71 g (32%) of the title compound as a white solid: mp discolors above 100° C., MS(−)ESI m/z 189 [M−H]−.

Provenance & Evidence