Water → 3-Methylsulfonamido-2-pyridinecarboxaldehyde

HRID 7155

Reaktionsgleichung

Reaktionsgleichung von HRID 7155
[CH3:1][S:2]([NH:5][C:6]1[C:7]([CH3:12])=[N:8][CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:3].O.[Se](=O)=[O:15]>O1CCOCC1>[CH3:1][S:2]([NH:5][C:6]1[C:7]([CH:12]=[O:15])=[N:8][CH:9]=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24007Selenium DioxideHCID 220186853-Methylsulfonamido-2-methylpyridine

Produkt 1

HCID 220186543-Methylsulfonamido-2-pyridinecarboxaldehydeAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 3-methylsulfonamido-2-methylpyridine (310 mg, 1.66 mmol) in dioxane (8 mL) was added water (0.8 mL) and selenium(IV) oxide (241 mg, 2.17 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/ethyl acetate, 1:1) to afford the title compound (278 mg, 83%). 1H NMR (CDCl3) □ 3.14 (s, 3H), 7.53 (dd, 1H, J=9, 6 Hz), 8.16 (dd, 1H, J=9, 3 Hz), 8.53 (dd, 1H, J=6, 3 Hz), 10.09 (s, 1H), 10.41 (br s, 1H, NH).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1781f000e508492c963f107d63b76858
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084155B2

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