[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:6]([NH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][N:13]=[CH:14]2)=[O:7].CO.[ClH:26]>[Pt]=O>[ClH:26].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:6]([NH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][NH:13][CH2:14]2)=[O:7]5-(3,4-dimethoxybenzamido) isoquinoline (2.7 g) was dissolved in 10% hydrochloric acid (100 ml) and methanol (100 ml) with warming. This was hydrogenated over platinum oxide (200 mg) at 45 psi. The catalyst was removed by filtration and the filtrate cooled in the refrigerator. A white precipitate formed and was collected by filtration and recrystallized from methanol to yield 2.1 g of 5-(3,4-dimethoxybenzamido)-1,2,3,4-tetrahydroisoquinoline hydrochloride as a white crystalline powder, m.p., 287°-288° C.
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