Sodium Hydroxide → HCID 15163460, compound

HRID 1789052Notes

Reaction equation

HRID 1789052 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([CH3:11])[C:4]=1[CH3:12].ClC1C=C(C=CC=1)C(OO)=[O:18].[OH-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N+:6]([O-:18])=[C:5]([CH3:11])[C:4]=1[CH3:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 15163513HCID 15163513, compound

Product 1

HCID 15163460HCID 15163460, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

6.3 g of 4,5-dimethoxy-2,3-dimethylpyridine are dissolved in 120 ml of methylene chloride, 20 g of m-chloroperoxybenzoic acid are added successively and the mixture is stirred first at 20° C. for 2 hours and then at 40° C. for 4 hours. After addition of 20 ml of 5N sodium hydroxide solution, the mixture is washed three times with a mixture of 5% strength sodium thiosulphate solution and 5% strength sodium carbonate solution, the aqueous phases are back-extracted twice with methylene chloride and the combined organic phases are dried over magnesium sulphate and concentrated. 4.6 g (66% of theory) of 4,5-dimethoxy-2,3-dimethylpyridine 1-oxide are obtained. The Rf value in methylene chloride/methanol 19:1 is 0.25.

Workup

  1. waitat 40° C. for 4 hours
  2. washthe mixture is washed three times
  3. additionwith a mixture of 5% strength sodium thiosulphate solution and 5% strength sodium carbonate solution
  4. extractionthe aqueous phases are back-extracted twice with methylene chloride
  5. dry with materialthe combined organic phases are dried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-63bcfa1627524035ab17caa52c67434b
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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