Sodium Hydroxide → 8-Quinolinamine, 6-bromo-

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To a solution of 6-bromo-8-nitro-quinoline (4 g, 1.58 mmol) in EtOH/HOAc/H2O (50 mL/50 mL/25 mL) was added iron metal (3.18 g, 5.69 mmol). The resulting solution was heated at reflux for 3 hours. The cooled reaction mixture was neutralized with 2.5 N NaOH, filtered through celite to remove iron solids and washed with EtOAc. The eluent was extracted into EtOAc (3×200 mL), combined, dried over NASO4 and concentrated. The resulting oil was purified by column chromatography (40% EtOAc/hexanes) affording 3.19 g (91%) of a yellow solid: mp 142-145° C.

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