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

HRID 272770Notes

Reaction equation

HRID 272770 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([O-])(O)=O.[Na+]>C(Cl)Cl.O>[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

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 7364875-Bromoisoquinoline

Product 1

HCID 22665708Isoquinoline, 5-bromo-, 2-oxideYield 75.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromoisoquinoline (0.83 g, 3.0 mmol), MCPBA (1.84 g, 8 mmol) and NaHCO3 (0.672 g, 8 mmol) in CH2Cl2 (10 mL) and H2O (5 mL) was stirred overnight. The solvents were removed, and the residue was purified by silica gel column chromatography eluting with EtOAc to give 0.51 g of the title compound. MS (APCI) m/e 225 (M+H)+.

Workup

  1. customThe solvents were removed
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with EtOAc

Sources & evidence

ORD record
ord-f4e7ca06c19e4478a76bc256f4af81ee
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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