m-Chloroperbenzoic acid → Isoquinoline, 7-bromo-1-chloro-, 2-oxide

HRID 2060366Notes

Reaction equation

HRID 2060366 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[Cl:12])=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N+:8]([O-:21])=[C:9]2[Cl:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 65020247-Bromo-1-Chloroisoquinoline

Product 1

HCID 58128286Isoquinoline, 7-bromo-1-chloro-, 2-oxideYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-bromo-1-chloroisoquinoline (4.0 g, 15.8 mmol) in DCM (100 mL) at 0° C. was added mCPBA (˜77%, 7.46 g, 33.3 mmol). The reaction was allowed to stir at room temperature for 24 hours, diluted with DCM (100 mL) and washed with 1N NaOH and brine. The DCM extracts were dried over Na2SO4, filtered, concentrated and chromatographed on silica eluting with 5 to 15% acetone/DCM to give the title compound (1.43 g). LRMS (M+H)+=258.0.

Workup

  1. washwashed with 1N NaOH and brine
  2. dry with materialThe DCM extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica eluting with 5 to 15% acetone/DCM

Sources & evidence

ORD record
ord-54cf877fe4fa455195b05d7d9d370657
Source dataset
uspto-grants-2012_10
Patent number
US08278322B2

Reaction notes

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