[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:18](=[O:19])[CH:17]=[C:16]([CH3:20])O[C:14]=3[CH3:21])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.Cl.[NH2:25][OH:26].C([O-])(=O)C.[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:18](=[O:19])[CH:17]=[C:16]([CH3:20])[N:25]([OH:26])[C:14]=3[CH3:21])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1A mixture of 3-(4-(4-chlorophenoxy)phenyl)-2,6-dimethylpyran-4-one (1.0 g), hydroxylamine hydrochloride (1.06 g), sodium acetate (1.25 g) and water (5 ml) in ethanol (10 ml) was heated at reflux for 3 days. After cooling to rt the mixture was diluted with water (20 ml) and the precipitate filtered off and washed with ethyl acetate. Recrystallisation from DMF afforded the title compound (0.2 g), m.p. 232°-236°, NMR δH (d6-DMSO)7.5-7.4 (2H, d, a 8 Hz), 7.3-7.2 (2H, d, J 8 Hz), 7.15-7.0 (4H, m), 6.75 (1H, s), 2.35 (3H, s), 2.15 (3H, s).
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