2-Methyl-5-hydroxypyridine → 6-Methyl-1-oxo-1lambda~5~-pyridin-3-ol

HRID 723527Notes

Reaction equation

HRID 723527 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:17])C=1>C(Cl)(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N+:6]([O-:17])[CH:7]=1

Participants

4

Reactant 2

HCID 142752-Methyl-5-hydroxypyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 904066-Methyl-1-oxo-1lambda~5~-pyridin-3-olYield 96.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-Hydroxy-2-methylpyridine (25 g) was suspended in chloroform (500 ml) and treated with m-chloroperbenzoic acid (57 g of material described as 57-86% pure). After stirring for 1 hour the solution was dried with MgSO4 and poured onto a silica column. Elution with EtOAc to remove byproducts and then with 20-50% EtOH in EtOAc gave the product (27.7 g).

Workup

  1. dry with materialwas dried with MgSO4
  2. additionpoured onto a silica column
  3. washElution with EtOAc
  4. customto remove byproducts

Sources & evidence

ORD record
ord-65c5ceab23894568a47bd5179f5ffc86
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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