1-Benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline → 1-Benzyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol

HRID 893325Notes

Reaction equation

HRID 893325 reaction equation
[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][C:14]([O:20]C)=[C:15]([O:18]C)[CH:16]=2)[CH2:11][CH2:10][NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Br>[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][C:14]([OH:20])=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10][NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 300241-Benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 1775111-Benzyl-1,2,3,4-tetrahydroisoquinoline-6,7-diolYield 83.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Treat 1-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (10 g) with 48% HBr (100 mL) and heat the mixture at reflux under nitrogen for 2 h. Cool the mixture to room temperature and allow crystals to form overnight. Collect the crystals and wash with cold ethanol to give 7.5 g of the title compound as its HBr salt, mp=233°-236° C.

Workup

  1. temperatureheat the mixture
  2. temperatureat reflux under nitrogen for 2 h
  3. customto form overnight
  4. customCollect the crystals
  5. washwash with cold ethanol

Sources & evidence

ORD record
ord-c9e1a9cce5a54e46a15f151c95fbf8b9
Source dataset
uspto-grants-1992_06
Patent number
US05124337

Reaction notes

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