6-Methoxyisoquinoline → Isoquinolin-6-ol

HRID 1194107Notes

Reaction equation

HRID 1194107 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N:8][CH:7]=[CH:6]2>Br>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N:8][CH:7]=[CH:6]2

Participants

3

Reactant 1

HCID 110409786-Methoxyisoquinoline

Product 1

HCID 135483582Isoquinolin-6-olYield 82.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

6-Methoxyisoquinoline (16 g, 0.1M) and 48% aqueous HBr (600 ml) were refluxed together for 6 hours and the mixture was then evaporated to dryness in vacuo. The residue was dissolved in H2O and basified with solid Na2CO3. The resulting precipitated solid was filtered off and recrystallised from isopropanol to give 6-hydroxyisoquinoline (12 g, 82%), m.p. 218°-20° C. (lit.* 220° C.).

Workup

  1. customthe mixture was then evaporated to dryness in vacuo
  2. dissolutionThe residue was dissolved in H2O and basified with solid Na2CO3
  3. customThe resulting precipitated solid
  4. filtrationwas filtered off
  5. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-f48251a4267c4fe8847ace4aca279c73
Source dataset
uspto-grants-1989_03
Patent number
US04812573

Reaction notes

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