[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:18][OH:19].C([O-])(=O)C.[Na+].O>C(O)C>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[N:18][OH:19])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]A solution of (4-formylphenyl)carbamic acid tert-butyl ester (1.0 g), hydroxylamine hydrochloride (0.31 g), and sodium acetate (0.37 g) in ethanol (8.5 mL)/water(1.5 mL) is heated at reflux temperature for 1 hour. The mixture is cooled to ambient temperature and partitioned between diethyl ether and water. The aqueous layer is back-extracted with diethyl ether and the combined organic extracts are washed with saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.8 g pure white solid as the product. MS: m/z 237 (M+H)+.
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