Реакция #332411

Уравнение реакции

Potassium hydroxide

5-fluoro-1H-indole-2,3-dione

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

→

6-fluoro-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

Выход 100.2%

Растворители

water

ethanol

Условия реакции

Обработка

1. 1
   Температураthe mixture was heated
2. 2
   Температураto reflux for 1 h
3. 3
   ДругоеThe solvent was removed under reduced pressure
4. 4
   workup.DISSOLUTIONthe residue was dissolved in water
5. 5
   Промывкаthe mixture was washed with ether (3 times)
6. 6
   ТемператураThe aqueous mixture was chilled
7. 7
   ФильтрацияThe solid was collected by filtration
8. 8
   Промывкаwashed with water, and air
9. 9
   Другоеdried

Методика

Potassium hydroxide (20.39 g, 363 mmol) in water (40 mL) was added to a suspension of 5-fluoro-1H-indole-2,3-dione (10.0 g, 60.6 mmol) in ethanol (100 mL) slowly. 1-[3-(Trifluoromethyl)phenyl]-1-propanone (12.24 g, 60.6 mmol) was added, and the mixture was heated to reflux for 1 h. The solvent was removed under reduced pressure, the residue was dissolved in water, and the mixture was washed with ether (3 times). The aqueous mixture was chilled and adjusted to pH˜3 with concentrated HCl. The solid was collected by filtration, washed with water, and air dried to afford 6-fluoro-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (21.2 g, >99% yield). MS (m/z) 350.1 (M+H+).

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