Ethanol → 2-(4-Cyclohexylphenyl)-6-fluoro-3-methylquinoline-4-carboxylic acid

HRID 1086823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1086823
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[CH2:13]1[CH2:18][CH2:17][CH:16]([CH:19]([CH3:28])[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24]C=2)=O)[CH2:15][CH2:14]1.[OH-:29].[K+].[CH2:31](O)C>O>[CH:16]1([C:19]2[CH:20]=[CH:22][C:27]([C:26]3[C:25]([CH3:24])=[C:5]([C:6]([OH:11])=[O:29])[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[N:7]=3)=[CH:31][CH:28]=2)[CH2:15][CH2:14][CH2:13][CH2:18][CH2:17]1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 2365665-FluoroisatinHCID 67928556HCID 67928556, Verbindung

Produkt 1

HCID 51671812-(4-Cyclohexylphenyl)-6-fluoro-3-methylquinoline-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

5-Fluoroisatin (100 g, 0.61 mole) and 4-cyclohexylpropiophenone (131 g, 0.61 mole) were suspended in 1100 ml of ethanol and stirred mechanically as a solution of 219 g (5.5 mole) of KOH in 550 ml of water was added dropwise. After the addition was complete, the mixture was heated at reflux for 12 hours, cooled, and the ethanol evaporated under reduced pressure. The resulting solid was dissolved in water and washed with ethyl ether. The aqueous layer was acidified with HCl. The resulting precipitate was filtered and dried. Recrystallization from dimethylformamide and water gave 117 g of 2-(4-cyclohexylphenyl)-6-fluoro3-methylquinoline-4-carboxylic acid, m.p. 316°-323°.

Aufarbeitung

  1. additionwas added dropwise
  2. additionAfter the addition
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 12 hours
  5. temperaturecooled
  6. customthe ethanol evaporated under reduced pressure
  7. dissolutionThe resulting solid was dissolved in water
  8. washwashed with ethyl ether
  9. filtrationThe resulting precipitate was filtered
  10. customdried
  11. customRecrystallization from dimethylformamide and water

Quellen und Nachweise

ORD-Eintrag
ord-67bf7149f9d8498f9d6d8c65f83a5e1d
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05032597

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