Selenium Dioxide → Ethyl 2-(6-formamidopyridin-2-yl)glyoxylate

HRID 1982679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1982679
[CH:1]([NH:3][C:4]1[N:9]=[C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:6][CH:5]=1)=[O:2].[Se](=O)=[O:17]>O1CCOCC1>[CH:1]([NH:3][C:4]1[N:9]=[C:8]([C:10](=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:6][CH:5]=1)=[O:2]

Komponenten

4

Edukt 2

HCID 24007Selenium DioxideHCID 13060164HCID 13060164, Verbindung

Produkt 1

HCID 13060174Ethyl 2-(6-formamidopyridin-2-yl)glyoxylateAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 2-(6-formamidopyridin-2-yl)acetate (26 g.) in dioxane (260 ml.) was added selenium dioxide (16.65 g.) in small portions at 85° to 90° C. over one hour and stirred at the same temperature for one hour. After cooling the resultant solution the dioxane layer was separated and concentrated under reduced pressure and then the residue was dissolved in ethyl acetate. The solution was washed with water, dried over magnesium sulfate and treated with activated charcoal and then concentrated under reduced pressure. The residue was triturated with diethyl ether to give ethyl 2-(6-formamidopyridin-2-yl)glyoxylate (14.3 g.), mp 124° to 126° C.

Aufarbeitung

  1. customwas separated
  2. concentrationconcentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with activated charcoal
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-06d4e8ac456b469bb9b79defa59db13b
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04596869

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