[C:1]1([C:7](=O)[CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+].O>CCO>[C:1]1([C:7](=[N:19][OH:20])[CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1To a solution of 1-phenyl-4-(pyridin-4-yl)butan-1-one (2.0 g, 8.7 mmol) in 20 mL of EtOH was added hydroxylamine hydrochloride (0.73 g, 10 mmol) and sodium acetate (1.4 g, 17 mmol). The reaction flask was heated at 80° C. for 4 h and was then cooled to room temperature. Addition of water and filtration of the resultant precipitate afforded 2.0 g (89%) of the title compound.
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