Sodium Sulfate → 5-Methoxy-2-methyl-1-oxo-1lambda~5~-pyridine

HRID 636648Notes

Reaction equation

HRID 636648 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=1.S([O-])([O-])(=O)=[O:11].[Na+].[Na+].ClC1C=C(C=CC=1)C(OO)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N+:3]=1[O-:11]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 70297m-Chloroperbenzoic acidHCID 133587775-Methoxy-2-methylpyridine

Product 1

HCID 122140195-Methoxy-2-methyl-1-oxo-1lambda~5~-pyridineYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-5-methoxy-pyridine (2.93 g, 24 mmol) in DCM (100 mL) was added sodium sulphate (5 g, 35 mmol), followed by m-chloro-peroxy-benzoic acid (10 g, 58 mmol), and mixture was stirred at room temperature for ˜48 hours. The reaction mixture was filtered, and the white solid was washed with DCM. The filtrate was concentrated and purified by normal phase chromatography eluting with a gradient of 1:1 EtOAc/heptane to EtOAc to give 2-methyl-5-methoxy-pyridine-N-oxide (2.41 g, 72%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe white solid was washed with DCM
  3. concentrationThe filtrate was concentrated
  4. custompurified by normal phase chromatography
  5. washeluting with a gradient of 1:1 EtOAc/heptane to EtOAc

Sources & evidence

ORD record
ord-91412f9e6d9b40d0bef4813eea30842c
Source dataset
uspto-grants-2001_02
Patent number
US06194437B1

Reaction notes

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