[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.Cl.[NH2:12][OH:13].CC([O-])=O.[Na+]>O.CCO>[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[N:12][OH:13])[CH3:9])=[CH:4][CH:3]=1To a 200-ml, round bottom flask was added, 1-(6-fluoropyridin-3-yl)ethanone (Method 65, 2.5 g, 17.9 mmol), hydroxylamine hydrochloride (2.5 g, 35.8 mmol), and NaOAc (3.7 g, 44.8 mmol) in a solution of water-EtOH (65 ml, 3.3:1). The resulting mixture was heated to 50° C. for 1 hour. The reaction was then allowed to cool to room temperature, partitioned with EtOAc, layers were cut, and organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound in quantitative yield. 1H NMR: 11.49 (s, 1H) 8.47 (s, 1H) 8.17-8.27 (m, 1H) 7.21 (dd, J=8.29, 3.01 Hz, 1H) 2.17 (s, 3H).
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