Hydrogen Peroxide → HCID 178433625, compound

HRID 1886178Notes

Reaction equation

HRID 1886178 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.[OH:11]O>C(O)(=O)C>[CH3:1][C:2]1[NH:10][C:5]2[CH:6]=[N:7][CH:8]=[CH:9][C:4]=2[N+:3]=1[O-:11]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 178432317HCID 178432317, compound

Product 1

HCID 178433625HCID 178433625, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the method of Chem. Pharm. Bull., 12, 866 (1964), a solution of 2-methylimidazo[4,5-c]pyridine (5.65 g, 42.5 mmol) in 30% aqueous hydrogen peroxide (15 ml) and glacial acetic acid was stirred at 60° C. for 6 days. The volatiles were removed under reduced pressure and the residue was dissolved in ethanol and treated with solid anhydrous potassium carbonate. The solid was filtered off, washed with ethanol, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography eluting with 10-30% water in acetone. Fractions containing the product were concentrated under reduced pressure, redissolved in isopropanol/toluene, 1:1 (200 ml) and re-evaporated to give the title compound, as a hygroscopic solid, (2.94 g, 46%).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethanol
  3. additiontreated with solid anhydrous potassium carbonate
  4. filtrationThe solid was filtered off
  5. washwashed with ethanol
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography
  8. washeluting with 10-30% water in acetone
  9. additionFractions containing the product
  10. concentrationwere concentrated under reduced pressure
  11. dissolutionredissolved in isopropanol/toluene
  12. custom1:1 (200 ml) and re-evaporated

Sources & evidence

ORD record
ord-bfbf3ecc339e4abf9b25df1aa1ac0d70
Source dataset
uspto-grants-1992_09
Patent number
US05149814

Reaction notes

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