Sodium Hydroxide → HCID 86710342, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-((tert-butoxycarbonyl)amino)-8-chloro-6-methylbenzo[c][2,7]naphthyridin-6-ium fluoride (0.35 g, 0.65 mmol) and NaOH (0.162 g, 4.06 mmol) in a mixture of DCM (10 mL) and water (10 mL) was added KMnO4 (0.642 g, 4.06 mmol) in portions at rt and the reaction was heated to 90° C. for 1 h. The solution was diluted with water (10 mL) and extracted with DCM (2×20 mL). The combined organic layers were washed with water 50 mL, dried over sodium sulfate, and concentrated under reduced pressure to yield (8-chloro-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-4-yl)carbamic acid (305 mg, 0.422 mmol, 65% yield) as a yellow solid, which carried on without further purification. LC/MS (ESI) m/e 304.1 [(M+H)+, calcd for C14H11ClN3O3 304.04]; LC/MS retention time (Method D): tR=1.01 min.

Provenance & Evidence