Reaktion #66712

Reaktionsgleichung

5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid

HCl

→

5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole

Ausbeute 53.0%

Lösungsmittel

EtOAc

quinoline

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated
2. 2
   Temperaturto reflux for 1.5 hours
3. 3
   Temperaturthe reaction mixture was refluxed for 1 hour
4. 4
   TemperaturThe reaction mixture was cooled
5. 5
   Extraktionextracted with EtOAc
6. 6
   WaschenThe combined organic layers were washed with brine
7. 7
   Trocknendried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    SonstigeThe residue was chromatographed (10% EtOAc/Hexanes)

Vorschrift

To a solution of 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid (2.0 g, 7 mmol) in 5 ml quinoline was added copper powder (50 mg), and the reaction mixture was heated to reflux for 1.5 hours. Copper powder (50 mg) was added, and the reaction mixture was refluxed for 1 hour. The reaction mixture was cooled, diluted with EtOAc, poured into 50 ml 6 N HCl, and extracted with EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed (10% EtOAc/Hexanes) to give 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole (850 mg, 51%) as a solid.

Quelle