tetrahydroisoquinoline was added 14 ml of 48 hydrobromic acid and the mixture was heated under reflux for 3 hours under an argon gas stream the reaction mixture was cooled and the crystals which separated ount were collected by filtration giving 540 mg of 7 8 dihydroxy 4 3 4 dihydroxyphenyl 1 2 3 4 tetrahydroisoquinoline hydrobromide elemental analysis as c 15 h 16 no 4 br ______________________________________ c h n br ______________________________________calcd 50 87 4 55 3 95 22 56found 51 02 4 33 3 96 22 82______________________________________ u03b4 ppm 3 24 1h m 3 52 1h m 6 08 1h d 6 48 1h dd 6 58 1h s 6 68 1h d 6 76 1h d 510 mg of u03b1 3 methoxy 2 methylbenzyl amino methyl 3 4 dimethoxybenzyl alcohol was dissolved in 3 8 ml of trifluoroacetic acid 0 12 ml of conc sulfuric acid was added dropwise under ice cooling and the mixture was allowed to react for 30 minutes the reaction solution was concentrated and subjected to azeotropic distillation with toluene 2 times the residue was dissolved in chloroform and basified by addition of 28 aqueous ammonia the chloroform layter was collected washed with water and dried over anhydrous magnesium sulfate the solvent was distilled off and the residue was recrystallized from ethyl acetate n hexane giving 430 mg of 7 methoxy 4 3 4 dimethoxyphenyl 8 methyl 1 2 3 4 tetrahydroisoquinoline m p 128.