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

HRID 346051

Reaktionsgleichung

Reaktionsgleichung von HRID 346051
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

With stirring, sodium pellets (3.95 g, 0.172 mol), maintained dry under hexane, were added to 540 ml dry methanol, under N2. Following dissolution, the mixture was diluted with 900 ml methanol, 4-nitro-2-methylpyridine 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+).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-03c21b2224684d0684ff0a449d751577
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05059609

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