7-Bromo-1-Chloroisoquinoline → 7-Bromoisoquinoline

HRID 14253

Reaction equation

HRID 14253 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-51725a07dc75426cb2d226d4e7ea7d78
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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