Potassium Hydroxide → 6-Fluoro-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245229

Reaktionsgleichung

Reaktionsgleichung von HRID 245229
[OH-:1].[K+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=O.[F:15][C:16]([F:28])([F:27])[C:17]1[CH:18]=[C:19]([C:23](=O)[CH2:24][CH3:25])[CH:20]=[CH:21][CH:22]=1>O.C(O)C>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:23]([C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:27])[F:28])[CH:18]=1)[C:24]([CH3:25])=[C:7]2[C:8]([OH:13])=[O:1]

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 137064Propiophenone, 3'-(trifluoromethyl)HCID 2365665-Fluoroisatin

Produkt 1

HCID 673838086-Fluoro-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. washthe mixture was washed with ether (3 times)
  6. temperatureThe aqueous mixture was chilled
  7. filtrationThe solid was collected by filtration
  8. washwashed with water, and air
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9efed4f656244defa2cf9c287b7caa9f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658636B2

Verknüpfte Notizen

Wird geladen…