Hydrochloric Acid → 4-Methoxy-2,3,5-trimethylpyridine 1-oxide

HRID 35469

Reaction equation

HRID 35469 reaction equation
[Na].[CH3:2][C:3]1[C:8]([CH3:9])=[C:7]([N+]([O-])=O)[C:6]([CH3:13])=[CH:5][N+:4]=1[O-:14].Cl.[CH3:16][OH:17]>C(OCC)(=O)C>[CH3:16][O:17][C:7]1[C:6]([CH3:13])=[CH:5][N+:4]([O-:14])=[C:3]([CH3:2])[C:8]=1[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 5360545SodiumHCID 112176114-Nitro-2,3,5-trimethylpyridine, 1-oxide

Product 1

HCID 107022374-Methoxy-2,3,5-trimethylpyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

22.6 g of sodium are dissolved in 4 1 of methanol under argon. 120 g of 2,3,5-trimethyl-4-nitropyridine 1-oxide are then added portionwise thereto and the solution is left to boil under reflux overnight. The pH is adjusted to 7 by means of 5N hydrogen chloride in ethyl acetate while cooling and the mixture is then evaporated in vacuo. The residue is taken up in 1.5 1 of methylene chloride, the solution is filtered throuqh siliceous earth, which is rinsed with 0.5 1 of methylene chloride, the combined filtrates are evaporated in vacuo and the residue is crystallized from petroleum ether. There is obtained 4-methoxy-2,3,5-trimethylpyridine 1-oxide of melting point 48°-50°.

Workup

  1. waitthe solution is left
  2. temperatureunder reflux overnight
  3. temperaturewhile cooling
  4. customthe mixture is then evaporated in vacuo
  5. filtrationthe solution is filtered throuqh siliceous earth, which
  6. washis rinsed with 0.5 1 of methylene chloride
  7. customthe combined filtrates are evaporated in vacuo
  8. customthe residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-518b8ecebb294c6991c42d564bd64b1a
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Linked notes

Loading…