Cl.[NH2:2][OH:3].[F:4][C:5]1[C:12]([I:13])=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O>C(O)C>[F:4][C:5]1[C:12]([I:13])=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[N:2][OH:3]A 50% aqueous solution of hydroxylamine hydrochloride (9 mL, 64.8 mmol) was added to a stirred suspension of 2-fluoro-3-iodobenzaldehyde (preparation 22d, 2.10 g, 8.4 mmol) in ethanol (10 mL) and the mixture was warmed slightly until a solution was formed. After stirring for 3 days at room temperature, the mixture was concentrated in vacuo and water was added to the residue. The mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried (MgSO4) and evaporated to give the title compound (2.15 g, 97%) as a solid.
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