m-Chloroperbenzoic acid → 4-Bromoisoquinoline N-oxide

HRID 501543Notes

Reaction equation

HRID 501543 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N+:4]([O-:20])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 737434-Bromoisoquinoline

Product 1

HCID 8173234-Bromoisoquinoline N-oxideYield 101.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 4-bromoisoquinoline (4.16 g, 18.6 mmol) in chloroform (100 mL) was added dropwise over 1 h to a solution of 70% mCPBA (12.4 g, 50.3 mmol) in chloroform (100 mL) at rt. After stirring 18 h, the reaction mixture was washed with 1 N NaOH (2×150 mL), dried (MgSO4) and concentrated under reduced pressure to afford compound 13A (4.23 g, 94%) as an off-white solid. 1H NMR (400 MHz, CDCl3) □8.71 (s, 1H), 8.43 (s, 1H), 8.09 (d, 1H, J=8 Hz), 7.70 (m, 3H).

Workup

  1. washthe reaction mixture was washed with 1 N NaOH (2×150 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5cd2fca73e724c8f82842f92a17f7e38
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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