Hydrochloric Acid → 3,4-Dimethoxy-2-methyl-1-oxo-1lambda~5~-pyridine

HRID 903359Notes

Reaction equation

HRID 903359 reaction equation
[CH3:1][O-:2].[Na+].F[C:5]1[C:6]([CH3:15])=[N+:7]([O-:14])[CH:8]=[CH:9][C:10]=1[N+]([O-])=O.Cl.[CH3:17][OH:18]>>[CH3:1][O:2][C:5]1[C:6]([CH3:15])=[N+:7]([O-:14])[CH:8]=[CH:9][C:10]=1[O:18][CH3:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 10942334Sodium Methoxide2×HCID 197911692-methyl-3-fluoro-4-nitropyridine-N-oxide

Product 1

HCID 107496473,4-Dimethoxy-2-methyl-1-oxo-1lambda~5~-pyridine

Procedure

A solution of sodium methoxide (from 0.535 g sodium) in dry methanol (40 ml) was added dropwise to a stirred suspension of 3-fluoro-2-methyl-4-nitropyridine N-oxide (2 g) in dry methanol (50 ml) and the mixture was stirred overnight. Additional sodium methoxide (from 0.053 g sodium) was added and the mixture was heated under reflux for 1 hour. The mixture was neutralised with hydrochloric acid and evaporated to dryness. The residue was extracted with chloroform and the extract was evaporated to dryness to give 3,4-dimethoxy-2-methylpyridine N-oxide.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customevaporated to dryness
  4. extractionThe residue was extracted with chloroform
  5. customthe extract was evaporated to dryness

Sources & evidence

ORD record
ord-c53ca8a9d96842ea8a3797ea8e9d596f
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

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