Hydrogen Peroxide → 1,10-phenanthroline 1-oxide

HRID 1180685Notes

Reaction equation

HRID 1180685 reaction equation
[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[OH:15]O>C(O)(=O)C>[N+:1]1([O-:15])[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 13181,10-Phenanthroline

Product 1

HCID 4289551,10-phenanthroline 1-oxideYield 70.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
55 °C

Procedure

Referring to scheme 7, a mixture of 30 g [1,10]phenanthroline, 26 g 30% hydrogen peroxide and 200 ml acetic acid was added to a flask, and the mixture was then heated to 50-60° C. and stirred overnight. After completion of reaction, the reaction mixture was cooled to room temperature, and vacuum distillated to remove acetic acid, and then 300 ml CH2Cl2 was added. Next, the solution was filtered to remove solids, and neutralized by adding K2CO3(aq). The organic layer was separated, concentrated, and purified by column chromatography with silca gel (Methanol), so as to obtain solids [1,10]phenanthroline-N-oxide (23 g, yield 70.4%).

Workup

  1. additionwas added to a flask
  2. customAfter completion of reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. customto remove acetic acid
  5. addition300 ml CH2Cl2 was added
  6. filtrationNext, the solution was filtered
  7. customto remove solids
  8. additionby adding K2CO3(aq)
  9. customThe organic layer was separated
  10. concentrationconcentrated
  11. custompurified by column chromatography with silca gel (Methanol)

Sources & evidence

ORD record
ord-99b06176d72849e2b3f520f8dab23473
Source dataset
uspto-grants-2007_10
Patent number
US07282586B1

Reaction notes

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