m-Chloroperbenzoic acid → HCID 178437532, compound

HRID 1492619Notes

Reaction equation

HRID 1492619 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:6]([N:12]=1)=[N:7][CH:8]=[CH:9][C:10]=2[CH3:11])[CH3:2].ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[NH:4][C:5]2[C:6]([N:12]=1)=[N+:7]([O-:21])[CH:8]=[CH:9][C:10]=2[CH3:11])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 186930362-ethyl-7-methyl-3H-Imidazo[4,5-b]pyridine

Product 1

HCID 178437532HCID 178437532, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 28 g (174 mmol) of 2-ethyl-7-methylimidazo[4,5-b]-pyridine (described in European Patent Application 400,974, 12 May, 90) and m-chloroperbenzoic acid (80-90%, 44.6 g) in CHCl3 (300 mL) was heated at reflux for 0.5 hours. The mixture was concentrated and purified (SiO2, 100% CH2Cl2 gradient to 30% CH2Cl2 /MeOH) to give 29.8 g of the title compound as a solid.

Workup

  1. temperatureat reflux for 0.5 hours
  2. concentrationThe mixture was concentrated
  3. custompurified (SiO2, 100% CH2Cl2 gradient to 30% CH2Cl2 /MeOH)

Sources & evidence

ORD record
ord-07f22e1641a64cba9ce8ad5a4080bf0b
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

Loading…