C[O:2][C:3]1[CH:4]=[C:5]([CH:11]2[C:20]3[C:15](=[C:16]([CH3:21])[CH:17]=[CH:18][CH:19]=3)[CH2:14][NH:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9]C.[BrH:22]>>[BrH:22].[OH:2][C:3]1[CH:4]=[C:5]([CH:11]2[C:20]3[C:15](=[C:16]([CH3:21])[CH:17]=[CH:18][CH:19]=3)[CH2:14][NH:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[OH:9]To 420 mg of 4-(3,4-dimethoxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline, was added 48% hydrobromic acid, and the mixture was heated under reflux for 3 hours. After about 10 minutes, the crystals becomes to be separated out. The reaction mixture was cooled, and the crystals were collected by filtration, giving 420 mg of 4-(3,4-dihydroxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide.
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