Water → 4-Bromo-1-hydroxyisoquinoline

HRID 1673096Notes

Reaction equation

HRID 1673096 reaction equation
[Br:1]Br.[OH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1.O.C(OCC)(=O)C>C(O)(=O)C.O1CCCC1>[Br:1][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([OH:3])=[N:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24408BromineHCID 178517620HCID 178517620, compound

Product 1

HCID 3197724-Bromo-1-hydroxyisoquinolineYield 80.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Bromine (1.78 ml, 34.5 mmol) was added to an ice-cooled solution of 1-hydroxyisoquinoline (5.01 g, 34.5 mmol) in acetic acid (50 ml), and this reaction mixture was stirred at room temperature for 2 hours. Water, ethyl acetate, and tetrahydrofuran were added, and the resulting reaction mixture was filtered through filter paper. The organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate and hexane to give the title compound (6.19 g).

Workup

  1. customthe resulting reaction mixture
  2. filtrationwas filtered
  3. filtrationthrough filter paper
  4. washThe organic layer was washed with saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-c05519ac6d7b44a3bf0c785fb1df40d2
Source dataset
uspto-grants-2011_08
Patent number
US07999090B2

Reaction notes

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