Hydrogen Peroxide → HCID 178526235, compound

HRID 345421Notes

Reaction equation

HRID 345421 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.OO.FC(F)(F)C(O)=[O:15]>C(O)(=O)C>[NH:1]1[C:9]2[CH:8]=[CH:7][N+:6]([O-:15])=[CH:5][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 6422Trifluoroacetic acidHCID 178419860HCID 178419860, compound

Product 1

HCID 178526235HCID 178526235, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
73 °C

Procedure

1H Imidazo[4,5-c]pyridine (4.0 g, 33.6 mmol) was dissolved in 60 ml of fresh acetic acid, heated to 73° C.±1° C. and to the solution was added 8.8 ml of 30% H2O2 (78 mmol). After stirring and heating at 73° C. for 24 hrs, an additional 5 ml of H2O2 was added as well as 1 ml of trifluoroacetic acid. Heating at 73° C. was continued for an additional 3 days. After concentrating, an aliquot NMR (D2O) shows a 2:1 product: starting material mixture. Concentration of the main reaction mixture was followed by trituration of the residue with 50 ml of acetonitrile. The filtered insolubles 1.6 g (35%) are pure N-oxide by TLC, (reverse phase, 9:1 H2O:THF) 200 MHz NMR (D2O, δ from TSP): 7.82 (1H, d, J=7 Hz) 8.21 (1H, d of d, J=7 Hz, J=1 Hz) 8.52 (1H, s) 8.84 (1H, d, J=1).

Workup

  1. temperatureheated to 73° C.±1° C. and to the solution
  2. temperatureHeating at 73° C.
  3. concentrationAfter concentrating

Sources & evidence

ORD record
ord-38fb3a246ee042288bb664a619037f1b
Source dataset
uspto-grants-1991_10
Patent number
US05057517

Reaction notes

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