Water → 1-(4-Isopropylphenyl)-1H-indole-2-carboxylic acid

HRID 730192

Reaktionsgleichung

Reaktionsgleichung von HRID 730192
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11].Br[C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.[Cu]=O>[CH:20]([C:17]1[CH:18]=[CH:19][C:14]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[C:2]2[C:10]([OH:12])=[O:11])=[CH:15][CH:16]=1)([CH3:22])[CH3:21]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 114621-Bromo-4-isopropylbenzeneHCID 72899Indole-2-carboxylic acid

Produkt 1

HCID 686999491-(4-Isopropylphenyl)-1H-indole-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14829Copper oxideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 128.8 g (0.8 mol) of 1H-indole-2-carboxylic acid, of 159.2 g (0.8 mol) of 4-bromocumene, of 111.6 g (0.808 mol) of potassium carbonate and of 8 g (0.1 mol) of copper oxide in 200 ml of dimethylformamide is stirred at reflux for 24 hours. After cooling, 6 l of water are added to the beige suspension obtained. The suspension is filtered and then the insoluble material is taken up in 1 l of a 5N hydrochloric acid solution. This mixture is extracted with 500 ml of dichloromethane. The organic phase is washed with water, dried over sodium sulfate and then concentrated under reduced pressure. After drying under reduced pressure, 204.4 g of a white solid are obtained, which solid is used as is in the following stage.

Aufarbeitung

  1. temperatureat reflux for 24 hours
  2. temperatureAfter cooling
  3. customobtained
  4. filtrationThe suspension is filtered
  5. extractionThis mixture is extracted with 500 ml of dichloromethane
  6. washThe organic phase is washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. dry with materialAfter drying under reduced pressure, 204.4 g of a white solid
  10. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-bbee076cae534871a625b9f1acbc638e
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582671B2

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