Ethanol → Ethyl 5-methoxyindole-2-carboxylate

HRID 505627

Reaktionsgleichung

Reaktionsgleichung von HRID 505627
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]([OH:18])=[O:17])=[CH:10]2.[CH2:19](O)[CH3:20]>>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10]2

Komponenten

4

Edukt 3

HCID 702EthanolHCID 204015-Methoxyindole-2-carboxylic acidHCID 24386Thionyl Chloride

Produkt 1

HCID 20926Ethyl 5-methoxyindole-2-carboxylate

Versuchsvorschrift

1.91 ml (26.15 mmol) of thionyl chloride are added dropwise with stirring at 0° C. to a solution of 1 g (5.23 mmol) of 5-methoxy-1H-indole-2-carboxylic acid in 52 ml of ethanol. The reaction mixture is heated at reflux for 2 hours and then it is cooled and concentrated under reduced pressure. The residue is taken up in 100 ml of ethyl acetate and this solution is washed with two times 50 ml of water and then with 50 ml of a saturated sodium chloride solution. The solution is dried over magnesium sulfate and filtered, and then the filtrate is concentrated under reduced pressure. 1.2 g of product are obtained, which product is used as is in the following stage.

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. temperatureit is cooled
  4. concentrationconcentrated under reduced pressure
  5. washthis solution is washed with two times 50 ml of water
  6. dry with materialThe solution is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1775f487b12a450c912bce09086a4594
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781477B2

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