Water → 2-Formylnicotinonitrile

HRID 7154

Reaktionsgleichung

Reaktionsgleichung von HRID 7154
[C:1]([C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].O.[Se](=O)=[O:12]>O1CCOCC1>[C:1]([C:3]1[C:4]([CH:9]=[O:12])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24007Selenium DioxideHCID 47383082-Methylpyridine-3-carbonitrile

Produkt 1

HCID 190294752-FormylnicotinonitrileAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 3-cyano-2-picoline (166 mg, 1.41 mmol) in dioxane (3 mL) was added water (0.2 mL) and selenium(IV) oxide (228 mg, 2.05 mmol) and the mixture stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (Hexanes/ether, 3:1 then 1:1) to afford the title compound (18 mg, 10%) as a pale yellow solid. 1H NMR (CDCl3): δ 7.69 (dd, 1H, J=9, 6 Hz), 8.20 (d, 1H, J=9 Hz), 9.00 (d, 1H, J=3 Hz), 10.13 (s, 1H).

Aufarbeitung

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by column chromatography on silica gel (Hexanes/ether, 3:1

Quellen und Nachweise

ORD-Eintrag
ord-c91b9e7b100246bd91748a1ae525db65
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084155B2

Verknüpfte Notizen

Wird geladen…