[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH:10]=O)=[CH:4][CH:3]=1.Cl.[NH2:18][OH:19]>CO>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)/[CH:10]=[N:18]/[OH:19])=[CH:4][CH:3]=1To a mixture of 3-(4-fluorophenoxy)benzaldehyde (3.0 g, 13.8 mmol, 1.0 eq) in methanol was added hydroxylamine hydrochloride (1.06 g, 15.2 mmol, 1.1 eq). The reaction mixture was stirred at ambient temperature for 12 h, before being concentrated in vacuo. The residue was taken in ethyl acetate and washed with water. The organic layer was dried with anhydrous Na2SO4 and concentrated to obtain the desired product (3 g, 94%). 1H NMR (400 MHz, DMSO-d6) δ 8.12 (s, 1H), 7.42-7.38 (t, 1H), 7.32-7.31 (d, 1H), 7.27-7.23 (t, 2H), 7.16 (s, 1H), 7.13-7.10 (m, 2H), 7.01-6.99 (m, 1H). MS (ESI): 232.2 (M+H)+.
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