Hydrogen Bromide → 1,2,3,4-Tetrahydroisoquinolin-8-ol

HRID 130935Notes

Reaction equation

HRID 130935 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][NH:10][CH2:9][CH2:8]2.Br>>[CH2:11]1[C:12]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[OH:2])[CH2:8][CH2:9][NH:10]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 129507478-Methoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 136352141,2,3,4-Tetrahydroisoquinolin-8-olYield 80.4%

Procedure

Combine 8-methoxy-tetrahydroisoquinoline (665.7 mg, 4.08 mmol) and 48% HBr at room temperature. Reflux the reaction for 3 hours and then cool to room temperature. Recrystallize the product from EtOH and diethyl ether to afford 754.2 mg, 3.28 mmol (80% yield) of the title compound as a tannish white solid: 1H NMR (500 MHz, DMSO-d6); 2.9 (2H, t, J=6.16, 5.86 Hz), 3.2-3.4 (2H, m), 4.0 (2H, s), 6.6-6.8 (2H, m), 7.0-7.1 (1H, m), 8.8-9.1 (2H, br m), 9.9 (1H, s); MS m/z 148 (M−1).

Workup

  1. customat room temperature
  2. temperatureReflux
  3. customthe reaction for 3 hours
  4. customRecrystallize the product from EtOH and diethyl ether

Sources & evidence

ORD record
ord-a311e64c5fcb45e9a84ba777ee5259c1
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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