m-Chloroperbenzoic acid → HCID 178526259, compound

HRID 868500Notes

Reaction equation

HRID 868500 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[N:10][C:3]=12.ClC1C=CC=C(C(OO)=[O:19])C=1>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N+:5]([O-:19])=[C:4]2[NH:8][CH:9]=[N:10][C:3]=12

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178478247HCID 178478247, compound

Product 1

HCID 178526259HCID 178526259, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-Chloro-3H-imidazo[4,5-b]pyridine (15 g, 97.7 mMol) was dissolved in 150 mL of glacial acetic acid and m-chloroperbenzoic acid (23 g, 131 mMol) was added in portions to the stirred solution. After 12 hours the solid was isolated and washed with ether. The solid was suspended in 400 mL of hot ethanol, stirred, and isolated. The product, 7-chloro-3H-imidazo[4,5-b]pyridine-4-oxide, was dried in vacuo. Yield 14.98 g (8.83 mMol, 90.4%); m.p. 200° C. (dec).

Workup

  1. customAfter 12 hours the solid was isolated
  2. washwashed with ether
  3. customisolated
  4. dry with materialThe product, 7-chloro-3H-imidazo[4,5-b]pyridine-4-oxide, was dried in vacuo

Sources & evidence

ORD record
ord-0a56a881bad44beea6cc96d5ffe81037
Source dataset
uspto-grants-1988_10
Patent number
US04780452

Reaction notes

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