Hydrogen Peroxide → HCID 178526235, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence