Sulfuric Acid → 4,5-Dimethoxy-2-methylpyridine 1-oxide

HRID 1789047Notes

Reaction equation

HRID 1789047 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][O:5][C:6]1[C:7]([N+]([O-])=O)=[CH:8][C:9]([CH3:13])=[N+:10]([O-:12])[CH:11]=1.S(=O)(=O)(O)O>CO>[CH3:1][O:2][C:7]1[C:6]([O:5][CH3:4])=[CH:11][N+:10]([O-:12])=[C:9]([CH3:13])[CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10942334Sodium MethoxideHCID 151634575-Methoxy-2-methyl-4-nitropyridine 1-oxide

Product 1

HCID 151634594,5-Dimethoxy-2-methylpyridine 1-oxideYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

20 ml of a 30% strength sodium methylate solution are added dropwise to a suspension of 16.9 g of 5-methoxy-2-methyl-4-nitropyridine 1-oxide in 170 ml of dry methanol and the mixture is stirred at 20° C. for 15 hours and then at 50° C. for 4 hours. The pH is brought to 7 by careful addition of concentrated sulphuric acid, while cooling with ice, the mixture is concentrated, the residue is extracted by stirring with 200 ml of methylene chloride, the insoluble constituents are filtered off, 10 ml of toluene are added and the mixture is concentrated to dryness again. 15.2 g (98% of theory) of 4,5-dimethoxy-2-methylpyridine 1-oxide are obtained as colourless crystals of m.p. 118°-121° C.

Workup

  1. waitat 50° C. for 4 hours
  2. temperaturewhile cooling with ice
  3. concentrationthe mixture is concentrated
  4. extractionthe residue is extracted
  5. stirringby stirring with 200 ml of methylene chloride
  6. filtrationthe insoluble constituents are filtered off
  7. addition10 ml of toluene are added
  8. concentrationthe mixture is concentrated to dryness again

Sources & evidence

ORD record
ord-6cb98f1b0b3442788680bb6f7d9b6d9a
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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