m-Chloroperbenzoic acid → 6-Bromoisoquinoline 2-oxide

HRID 404717Notes

Reaction equation

HRID 404717 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.ClC1C=C(C(OO)=[O:20])C=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N+:7]([O-:20])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 3136816-BromoisoquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 222501786-Bromoisoquinoline 2-oxideYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 51.0 g (245.1 mmol) of 6-bromo-isoquinoline (3) in 800 ml of dichloromethane were added under mechanical stirring 90.6 g (367.6 mmol) of 3-chloro-benzenecarboperoxoic acid (70%). After stirring for 4 h at room temperature and standing overnight, saturated sodium hydrogen carbonate-solution was added until two clear layers were obtained. The dichloromethane solution was separated and washed with saturated NaCl-solution. The aqueous layers were extracted with a chloroform/isopropanol (3:1) mixture and the organic layers were combined, washed again with saturated NaCl-solution, dried over magnesium sulfate and evaporated. The obtained crude product (53.0 g) was used without further purification. Rt=0.89 min (Method C). Detected mass: 226.2 (M+H+).

Workup

  1. waitstanding overnight
  2. customwere obtained
  3. customThe dichloromethane solution was separated
  4. washwashed with saturated NaCl-solution
  5. extractionThe aqueous layers were extracted with a chloroform/isopropanol (3:1) mixture
  6. washwashed again with saturated NaCl-solution
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-d12272df49a0478d97c47b54b3fc2baf
Source dataset
uspto-grants-2014_06
Patent number
US08748614B2

Reaction notes

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