Propionic Acid → HCID 178437532, compound

HRID 1646065Notes

Reaction equation

HRID 1646065 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].C(O)(=[O:16])CC.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[NH:4][C:5]2[C:6]([N:12]=1)=[N+:7]([O-:16])[CH:8]=[CH:9][C:10]=2[CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 70297m-Chloroperbenzoic acidHCID 186930362-ethyl-7-methyl-3H-Imidazo[4,5-b]pyridine

Product 1

HCID 178437532HCID 178437532, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 28 g (174 mmol) of 2-ethyl-7-methylimidazo[4,5-b]pyridine prepared according to Example 2, Steps A and B, but substituting propionic acid in place of butyric acid in Step B (described in European Patent Application #400,974, May 12, 1990) 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. temperaturewas heated
  2. temperatureat reflux for 0.5 hours
  3. concentrationThe mixture was concentrated
  4. custompurified (SiO2, 100% CH2Cl2 gradient to 30% CH2Cl2 /MeOH)

Sources & evidence

ORD record
ord-7a4f2e59b80b407db6bbc46a5a1588fa
Source dataset
uspto-grants-1993_01
Patent number
US05177074

Reaction notes

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