m-Chloroperbenzoic acid → Isoquinoline, 5-bromo-, 2-oxide

HRID 2356362Notes

Reaction equation

HRID 2356362 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N+:6]([O-:20])=[CH:7]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 7364875-Bromoisoquinoline

Product 1

HCID 22665708Isoquinoline, 5-bromo-, 2-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromoisoquinoline (10.65 g, 51.19 mmol) in CH2Cl2 (250 mL), m-CPBA (9.717 g, 56.31 mmol) was added and the mixture refluxed for 20 h and allowed to cool to rt. The mixture was washed with sat Na2SSO3 (75 mL), then 3×1N NaOH, then brine. The organic layer was dried w/Na2SO4, filtered and evaporated. The residue was crystallized from CH2Cl2: Et2O to yield the title compound as a white fluffy solid (4.58 g). MS (ESI pos. ion) m/z: 224 (MH+). Calc'd exact mass for C9H5BrNO: 224.

Workup

  1. temperaturethe mixture refluxed for 20 h
  2. washThe mixture was washed with sat Na2SSO3 (75 mL)
  3. dry with materialThe organic layer was dried w/Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from CH2Cl2

Sources & evidence

ORD record
ord-5b158ee68e394e3db4f2ff66ab53aec3
Source dataset
uspto-grants-2010_07
Patent number
US07759344B2

Reaction notes

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