Hydrogen Bromide → 4,4-Dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol

HRID 277894Notes

Reaction equation

HRID 277894 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12]C)[CH:10]=2)[CH2:5][NH:4][CH2:3]1.Br>>[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[CH2:5][NH:4][CH2:3]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 122832086-Methoxy-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 122832244,4-Dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol

Procedure

A mixture of 4,4-dimethyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline (23.9 g, 0.125 mol) and 48% aqueous hydrobromic acid (158 ml) were heated at vigorous reflux for 4 hours. The reaction mixture was cooled and evaporated in vacuo. The residue was triturated with diethyl ether (20 ml), 1:1 diethyl ether:thf (20 ml) and diethyl ether (3×20 ml) and dried in vacuo to afford the title compound as the hydrobromide salt (17.5 g, 53%).

Workup

  1. temperaturewere heated
  2. temperatureat vigorous reflux for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. customevaporated in vacuo
  5. customThe residue was triturated with diethyl ether (20 ml), 1:1 diethyl ether
  6. dry with materialthf (20 ml) and diethyl ether (3×20 ml) and dried in vacuo

Sources & evidence

ORD record
ord-345688938f544416823b06572b186a49
Source dataset
uspto-grants-2002_03
Patent number
US06358974B1

Reaction notes

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