Ethyl Acetate → 1-(4-Bromo-phenyl)-isoquinolin-6-ol

HRID 342217

Reaction equation

HRID 342217 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18]C)=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C(OCC)(=O)C>C(O)(=O)C.Br>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 111415351-(4-Bromo-phenyl)-6-methoxy-isoquinoline

Product 1

HCID 1361286691-(4-Bromo-phenyl)-isoquinolin-6-ol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

The 1-(4-bromo-phenyl)-6-methoxy-isoquinoline obtained is boiled under reflux in 53 ml of acetic acid and 37 ml of 62% aqueous hydrobromic acid. Subsequently, after cooling to room temperature and addition of 150 ml of ethyl acetate the separated precipitate is filtered off. The crystals are washed with ethyl acetate and dried. There are obtained 7.6 g of 1-(4-bromo-phenyl)-isoquinolin-6-ol, MS: m/e 300 (M+H+, 1 Br).

Workup

  1. filtrationis filtered off
  2. washThe crystals are washed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-86d1d6104c494dc4936bdd7625021dfe
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Linked notes

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