Selenium Dioxide → 3-Nitropicolinaldehyde

HRID 1445003

Reaktionsgleichung

Reaktionsgleichung von HRID 1445003
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Se](=O)=[O:12]>O1CCOCC1>[CH:1]([C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)=[O:12]

Komponenten

4

Edukt 2

HCID 24007Selenium DioxideHCID 3293602-Methyl-3-nitropyridine

Produkt 1

HCID 3293613-NitropicolinaldehydeAusbeute 116,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 2-methyl-3-nitropyridine (10.155 g, 72.46 mmol) prepared in Step 1 of Preparation 1 and selenium dioxide (8.84 g, 79.71 mmol) in 1,4-dioxane (80 ml) was refluxed for 2 days. The reaction mixture was cooled to room temperature, filtered, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/2, v/v) to give 12.8 g of the titled compound as red oil.

Aufarbeitung

  1. temperaturewas refluxed for 2 days
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/2, v/v)

Quellen und Nachweise

ORD-Eintrag
ord-224b036d218d4c66bd5a4bee7179a438
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662832B2

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