Thionyl Chloride → 3-chlorocarbonyl-1-(6-methoxyquinol-4-yl)-1H-indole hydrochloride

HRID 1869168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869168
S(Cl)([Cl:3])=O.[C:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:9]=1)(O)=[O:6]>>[ClH:3].[Cl:3][C:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:9]=1)=[O:6]

Komponenten

3

Edukt 2

HCID 24386Thionyl ChlorideHCID 689705471-(6-Methoxyquinolin-4-yl)-1H-indole-3-carboxylic acid

Produkt 1

HCID 865948023-chlorocarbonyl-1-(6-methoxyquinol-4-yl)-1H-indole hydrochloride

Versuchsvorschrift

4 cm3 of thionyl chloride are added to 0.57 g (1.79 mmol) of 3-carboxy-1-(6-methoxyquinol-4-yl)-1H-indole under an argon atmosphere. After stirring at reflux for 2 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), successively triturated three times with 30 cm3 of dichloromethane and then concentrated to dryness under reduced pressure (2.7 kPa) to give 0.67 g of 3-chlorocarbonyl-1-(6-methoxyquinol-4-yl)-1H-indole hydrochloride in the form of a yellow powder which is used directly in the following step.

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customsuccessively triturated three times with 30 cm3 of dichloromethane
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-1c19062694e74324a04f8e9c334500dd
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638521B2

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