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

HRID 131020

Reaction equation

HRID 131020 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-d2dbbf431f6444498cabd91ee04aa236
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Linked notes

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