m-Chloroperbenzoic acid → HCID 86723762, compound

HRID 577533Notes

Reaction equation

HRID 577533 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[C:9]([CH3:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C1C=C(Cl)C=C(C(OO)=[O:25])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]([CH3:14])[CH3:15])[C:9]([CH3:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][N+:6]([O-:25])=[CH:7]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86723760HCID 86723760, compound

Product 1

HCID 86723762HCID 86723762, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-8-methyl-7-(propan-2-yloxy)isoquinoline (108e, 1.60 g, 5.71 mmol) in DCM (40 mL) was added m-CPBA (1.47 g, 8.56 mmol) and the reaction mixture was stirred at room temperature for 10 hours. The reaction mixture was washed with NaHSO3 (aq., 2×20 mL), 10% aq. NaOH (2×20 mL) and brine (2×10 mL), dried over Na2SO4, and concentrated under vacuum to give 5-bromo-8-methyl-7-(propan-2-yloxy)isoquinoline 2-oxide (108f, 1.3 g, 77%) as a brown solid.

Workup

  1. washThe reaction mixture was washed with NaHSO3 (aq., 2×20 mL), 10% aq. NaOH (2×20 mL) and brine (2×10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b86b207141f94035b4de9fbb660254b2
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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