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

HRID 979860Notes

Reaction equation

HRID 979860 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.[CH2:16]([OH:18])[CH3:17]>C(OCC)(=O)C>[CH2:16]([O:18][C:7]1[C:6]([CH3:13])=[CH:5][N+:4]([O-:14])=[C:3]([CH3:2])[C:8]=1[CH3:9])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5360545SodiumHCID 112176114-Nitro-2,3,5-trimethylpyridine, 1-oxide

Product 1

HCID 221514664-Ethoxy-2,3,5-trimethylpyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4.2 g of sodium were dissolved in 780 ml of ethanol under argon. 22.3 g of 2,3,5-trimethyl-4-nitropyridine 1-oxide were then added portionwise thereto and the solution was left to boil under reflux overnight. The pH was adjusted to 7 by means of 5N hydrogen chloride in ethyl acetate while cooling and the mixture was then evaporated in vacuo. The residue was taken up in 0.5 l of methylene chloride, the solution was filtered through silica gel, which was rinsed with 200 ml of methylene chloride, the combined filtrates were evaporated in vacuo and the residue was crystallized from petroleum ether. There was obtained 4-ethoxy-2,3,5-trimethylpyridine 1-oxide of melting point 59°-61°.

Workup

  1. waitthe solution was left
  2. temperatureunder reflux overnight
  3. temperaturewhile cooling
  4. customthe mixture was then evaporated in vacuo
  5. filtrationthe solution was filtered through silica gel, which
  6. washwas rinsed with 200 ml of methylene chloride
  7. customthe combined filtrates were evaporated in vacuo
  8. customthe residue was crystallized from petroleum ether

Sources & evidence

ORD record
ord-3cb9405c5b2d48eda81d81e2948d04fb
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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