Hydrogen Peroxide → 8-Bromoisoquinoline 2-oxide

HRID 1437356Notes

Reaction equation

HRID 1437356 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2.[OH:12]O>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N+:9]([O-:12])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 98591348-Bromoisoquinoline

Product 1

HCID 687005028-Bromoisoquinoline 2-oxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 8-bromo-isoquinoline (prepared by the method of F. T. Tyson, J.A.C.S., 1939, 61, 183) (1.25 g, 6 mmol) in acetic acid (5 ml) was treated with 27% aqueous hydrogen peroxide solution (1.8 ml) and heated at 75° C. overnight. The mixture was evaporated and the residue partitioned between aqueous sodium carbonate solution and dichloromethane, re-extracting with dichloromethane twice more. The combined organic extracts were dried and evaporated. The residue was triturated with ether/petrol and isolated by filtration (1.14 g, 85%).

Workup

  1. customThe mixture was evaporated
  2. customthe residue partitioned between aqueous sodium carbonate solution and dichloromethane
  3. extractionre-extracting with dichloromethane twice more
  4. customThe combined organic extracts were dried
  5. customevaporated
  6. customThe residue was triturated with ether/petrol
  7. customisolated by filtration (1.14 g, 85%)

Sources & evidence

ORD record
ord-1dabc35d9b6a47e3b636d160936d5503
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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