Sulfuric Acid → 4-(3,4-Dimethoxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1089476Notes

Reaction equation

HRID 1089476 reaction equation
CO[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][NH:6][CH2:7][CH:8](O)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1.S(=O)(=O)(O)O.F[C:30](F)(F)C(O)=O>>[CH3:18][O:17][C:11]1[CH:10]=[C:9]([CH:8]2[C:3]3[C:4](=[C:20]([CH3:30])[CH:21]=[CH:22][CH:23]=3)[CH2:5][NH:6][CH2:7]2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 20531701HCID 20531701, compound

Product 1

HCID 105170974-(3,4-Dimethoxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline

Procedure

900 mg of α-[[(2-methoxybenzylamino]methyl]-3,4-dimethoxybenzyl alcohol was dissolved in 7 ml of trifluoroacetic acid, and after adding thereto 0.21 ml of conc. sulfuric acid under ice cooling, the mixture was allowed to react for 60 minutes. The reaction solution was concentrated, and subjected to zzeotropic distillation 3 times, and after adding chloroform, the mixture was basified by addtion of 28% aqueous ammonia. By a separating procedure, the chloroform layer was collected, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue obtained was recrystallized from ethyl acetate-n-hexane, giving 440 mg of 4-(3,4-dimethoxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline, m.p. 86°-88° C.

Workup

  1. additionafter adding
  2. customto react for 60 minutes
  3. concentrationThe reaction solution was concentrated
  4. distillationsubjected to zzeotropic distillation 3 times
  5. additionafter adding chloroform
  6. customBy a separating procedure, the chloroform layer was collected
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customthe residue obtained
  11. customwas recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-542f1fa138af4b57a0c42da0311abf66
Source dataset
uspto-grants-1990_10
Patent number
US04966904

Reaction notes

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