Acetic Acid → 2-Methyl-4-methoxypyridine-N-oxide

HRID 610396Notes

Reaction equation

HRID 610396 reaction equation
[Na].[N+]([C:5]1[CH:10]=[CH:9][N+:8]([O-:11])=[C:7]([CH3:12])[CH:6]=1)([O-])=O.[C:13](O)(=[O:15])C.C([O-])(O)=O.[Na+]>CO.O>[CH3:13][O:15][C:5]1[CH:10]=[CH:9][N+:8]([O-:11])=[C:7]([CH3:12])[CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 95291Pyridine, 2-methyl-4-nitro-, 1-oxideHCID 516892Sodium BicarbonateHCID 5360545Sodium

Product 1

HCID 107018932-Methyl-4-methoxypyridine-N-oxide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

With stirring, sodium pellets (3.95 g, 0.172 mol), maintained dry under hexane, were added to 540 ml dry methanol, under N2. Following dissolutions the mixture was diluted with 900 ml methanol, 4-nitro-2-methyl-pyridine N-oxide (26.0 g, 0.169 mol) was added, and the mixture heated at reflux for 1 hour, cooled to room temperature and acidified with 18 ml glacial acetic acid. After stirring 15 minutes, the reaction mixture was stripped of solvent, the orange residue taken up in 300 ml of H2O, neutralized with saturated NaHCO3, reconcentrated to dryness, and the residue triturated 5×50 ml of ethanol. The ethanol triturates were combined, stripped to dryness, and the residue restripped 3×50 ml toluene to yield solids (36.1 g) which were chromatographed on silica gel using 6:1 CH2Cl2 :CH3OH as eluant to yield purified title product, 21.14 g; MS 139 M+).

Workup

  1. customdry under hexane
  2. additionwere added to 540 ml dry methanol, under N2
  3. additionwas added
  4. temperaturethe mixture heated
  5. temperatureat reflux for 1 hour
  6. stirringAfter stirring 15 minutes
  7. customthe residue triturated 5×50 ml of ethanol

Sources & evidence

ORD record
ord-601353d1b85f4df8a837e7e9dd3c1481
Source dataset
uspto-grants-1999_12
Patent number
US05998451

Reaction notes

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