C([N:8]1[CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([OH:25])[CH:19]=2)[C:15]2[C:10](=[C:11]([NH:27][CH:28]=[O:29])[C:12]([OH:26])=[CH:13][CH:14]=2)[CH2:9]1)C1C=CC=CC=1.[ClH:30]>C(O)C.[C].[Pd]>[ClH:30].[OH:25][C:20]1[CH:19]=[C:18]([CH:16]2[C:15]3[C:10](=[C:11]([NH:27][CH:28]=[O:29])[C:12]([OH:26])=[CH:13][CH:14]=3)[CH2:9][NH:8][CH2:17]2)[CH:23]=[CH:22][C:21]=1[OH:24]450 mg of 2-benzyl-4-(3,4-dihydroxyphenyl)-8-formamido-7-hydroxy-1,2,3,4-tetrahydroisoquinoline was dissolved in 9 ml of ethanol, and after adding thereto 0.86 ml of 2N hydrochloric acid, 0.05 g of 10% palladium-carbon, hydrogenation reaction was performed at room temperature. The hydrogenation reaction was over, the reaction mixture was filtered, and concentrated. The residue was changed to precipitates with treatment of isopropyl alcohol and acetonitrile, and the precipitates were collected by filtration, affording 320 mg of 4-(3,4-dihydroxyphenyl)-8-formamido-7-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride.
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