Hydrogen Bromide → 1,2,3,4-Tetrahydroisoquinolin-6-ol

HRID 492627Notes

Reaction equation

HRID 492627 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.Br>>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 266981,2,3,4-Tetrahydroisoquinolin-6-olYield 100%

Procedure

Combine 6-Methoxy-1,2,3,4-tetrahydro-isoquinoline (5.0, 20.5 mmol) and 48% HBr(aq), 20 ml at room temperature. After the reaction refluxes for 24 hours, cool the reaction to room temperature and concentrate under reduced pressure. Triturate with ethyl acetate and filter to afford 5.5 g, 20.5 mmol (99% yield) of the title compound as a tan solid: 1H NMR (500 MHz, DMSO); 2.8-2.9 (2H, m), 3.3-3.4 (2H, m), 4.1 (2H, s), 6.5-6.7 (2H, m), 6.9-7.1 (1H, m), 8.8-9.0 (2H, br s), 9.4-9.5 (1H, s).

Workup

  1. customat room temperature
  2. temperaturecool
  3. customthe reaction to room temperature
  4. concentrationconcentrate under reduced pressure
  5. customTriturate with ethyl acetate
  6. filtrationfilter

Sources & evidence

ORD record
ord-57b39e697d9b41bc991be125e0582f9b
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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