7-Bromo-1-Chloroisoquinoline → 7-Bromoisoquinoline

HRID 349043Notes

Reaction equation

HRID 349043 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2Cl)=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 65020247-Bromo-1-Chloroisoquinoline

Product 1

HCID 122574417-BromoisoquinolineYield 86.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 7-bromo-1-chloroisoquinoline (2.50 g, 10.3 mmol) and activated zinc (1.40 g, 21.65 mmol) in acetic acid (20 mL) was heated at reflux for 2 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide 7-bromoisoquinoline (1.86 g): ESI MS m/z 208 [M+H]+.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated sodium chloride
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4926c523b5ce4472ac7c413e171d201a
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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