Selenium Dioxide → 3-Nitropicolinaldehyde

HRID 473402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473402
[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>[N+:8]([C:7]1[C:2]([CH:1]=[O:12])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Komponenten

4

Edukt 2

HCID 24007Selenium DioxideHCID 3293602-Methyl-3-nitropyridine

Produkt 1

HCID 3293613-Nitropicolinaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-Methyl-3-nitropyridine (24 g, 173.91 mmol) was dissolved in 1,4-dioxane (500 mL) and to the mixture was added selenium dioxide (23 g, 208.7 mmol) and the mixture was heated under reflux for 16 h. After completion of reaction, the mixture was cooled to rt and filtered through Celite™ and the filtrate was concentrated under reduced pressure to give thick oily mass. The oily mass was purified by silical gel column chromatography using 20% of ethyl acetate and hexane as eluent to give 3-nitro-2-pyridinecarbaldehyde as an off white solid: 1H-NMR (CDCl3) δ: 7.7 (m, 1H), 8.3 (d, 1H), 9.0 (d, 1H), 10.3 (s, 1H).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 h
  3. customAfter completion of reaction
  4. filtrationfiltered through Celite™
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give thick oily mass
  7. customThe oily mass was purified by silical gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6125dbff90ba4f408de676406cbf1884
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633313B2

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