Sodium Hydroxide → 2-amino-4-fluoro-N-methoxybenzamide

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Reaction Steps

NMR Spectrum: (DMSO-d6) 6.88 (dd, 1H), 7.21 (ddd, 1H), 8.00 (dd, 1H), 11.87 (s, 1H). 7-fluoro-1H-3,1-benzoxazine-2,4-dione (0.85 g, 4.69 mmol) was added to stirred solution of O-methylhydroxylamine hydrochloride (1.960 g, 23.47 mmol) in a 2N aqueous solution of sodium hydroxide (11.73 ml, 23.47 mmol) at 25° C. The resulting solution was stirred at room temperature for 2 hours. The solution was diluted with EtOAc, washed sequentially with water and brine. The organic layer was dried over magnesium sulfate and evaporated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 5% MeOH in DCM to afford 2-amino-4-fluoro-N-methoxybenzamide (0.390 g, 45.1%) as a white crystalline solid. NMR Spectrum: (DMSOd6) 3.67 (s, 3H), 6.30 (dd, 1H), 6.47 (ddd, 1H), 6.62 (bs, 2H), 7.37 (dd, 1H), 11.40 (s, 1H)

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