Hydrochloric Acid → 4-Methoxy-2,5-dimethylpyridine 1-oxide

HRID 979866Notes

Reaction equation

HRID 979866 reaction equation
[Na].[CH3:2][C:3]1[CH:8]=[C:7]([N+]([O-])=O)[C:6]([CH3:12])=[CH:5][N+:4]=1[O-:13].Cl.[CH3:15][OH:16]>C(OCC)(=O)C>[CH3:15][O:16][C:7]1[C:6]([CH3:12])=[CH:5][N+:4]([O-:13])=[C:3]([CH3:2])[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 146707Pyridine, 2,5-dimethyl-4-nitro-, 1-oxideHCID 5360545Sodium

Product 1

HCID 151634614-Methoxy-2,5-dimethylpyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

12.2 g of sodium were dissolved in 2 l of methanol under argon, whereupon 60 g of 2,5-dimethyl-4-nitropyridine 1-oxide were added portionwise and the solution was left to boil under reflux overnight. The pH was adjusted to 7 with 5N hydrogen chloride in ethyl acetate while cooling and the mixture was evaporated in vacuo. The residue was taken up in 1 l of methylene chloride, the solution was filtered through silica gel, which was rinsed with 0.4 l of methylene chloride, and the combined filtrates were evaporated in vacuo. The residue crystallized from methylene chloride/petroleum ether and there was obtained 4-methoxy-2,5-dimethylpyridine 1-oxide of melting point 99°-101°.

Workup

  1. additionwere added portionwise
  2. waitthe solution was left
  3. temperatureunder reflux overnight
  4. temperaturewhile cooling
  5. customthe mixture was evaporated in vacuo
  6. filtrationthe solution was filtered through silica gel, which
  7. washwas rinsed with 0.4 l of methylene chloride
  8. customthe combined filtrates were evaporated in vacuo
  9. customThe residue crystallized from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-014c5fed39964517b99d04317c0ee057
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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