Selenium Dioxide → HCID 17974702, Verbindung

HRID 900747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 900747
[Se](=O)=[O:2].[Cl:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[CH3:15])=[CH:12][CH:11]=[CH:10][CH:9]=2>O1CCOCC1.O>[Cl:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[CH:15]=[O:2])=[CH:12][CH:11]=[CH:10][CH:9]=2

Komponenten

5

Edukt 2

HCID 24007Selenium DioxideHCID 92597Quinoline, 3-chloro-4-methyl-

Produkt 1

HCID 17974702HCID 17974702, VerbindungAusbeute 37,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of selenium dioxide (1.90 g) in 1,4-dioxan (5 ml) and water (1.2 ml) was added dropwise over 15 min to a stirred solution of 3-chloro-4-methylquinoline (2.91 g) in 1,4-dioxan (10 ml) at 60-70° C. The mixture was heated at reflux for 6 h, allowed to warm to room temperature, then concentrated in vacuo. The residue was purified by column chromatography (SiO2), eluting with dichloromethane to 5% methanol in dichloromethane by a stepwise gradient, to give the sub-title compound as a yellow solid (1.19 g).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (SiO2)
  5. washeluting with dichloromethane to 5% methanol in dichloromethane by a stepwise gradient

Quellen und Nachweise

ORD-Eintrag
ord-ed0566c55bec47bf9f1bf05e43d9d6bf
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361660B2

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