Reaktion #332331

Reaktionsgleichung

5-bromo-6-(methyloxy)-1H-indole-2,3-dione

KOH

1-[3-(trifluoromethyl)phenyl]-1-propanone

→

6-bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

Ausbeute 44.2%

Lösungsmittel

EtOH

EtOH

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter refluxing for 16 h
2. 2
   Sonstigethe mixture was evaporated
3. 3
   Sonstigeto remove EtOH
4. 4
   Filtrationfiltration
5. 5
   Sonstigeto yield the crude product
6. 6
   Filtrationfiltered
7. 7
   Sonstigedried

Vorschrift

A solution of 5-bromo-6-(methyloxy)-1H-indole-2,3-dione (75 g, 293 mmol), KOH (98.5 g, 1760 mmol) in EtOH (500 mL) and H2O (150 mL) was stirred followed by the addition of 1-[3-(trifluoromethyl)phenyl]-1-propanone (59 g, 293 mmol) in one portion. After refluxing for 16 h, the mixture was evaporated to remove EtOH and pH adjusted to 3 with 2N HCl. Following filtration to yield the crude product, the material was refluxed in EtOH (1 L) for 1 h, filtered and dried to yield 6-bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (57 g, 44% yield) as an off white solid. MS (m/z) 440 (M+H+).

Quelle