[CH3:1][N:2]([CH3:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>Br>[CH3:1][N:2]([CH3:19])[C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[O:10])=[CH:7][CH:8]=1A solution of 10.0 g 1-[4-(dimethylamino)phenyl]-1-(4-methoxyphenyl)-methanone in 30 ml 48% hydrobromic acid was heated at reflux for 21 hours. The reaction mixture was poured into aqueous sodium bicarbonate and the precipitate filtered. Recrystallization from 150 ml of methanol gave 7.3 g of white solid, m.p. 199°-200° C.
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