Isatin → 2-(3,4-Difluorophenyl)-4-quinolinecarboxylic acid

HRID 411514

Reaktionsgleichung

Reaktionsgleichung von HRID 411514
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=O)[C:2]1=[O:11].[F:12][C:13]1[CH:14]=[C:15]([C:20](=O)[CH3:21])[CH:16]=[CH:17][C:18]=1[F:19].[OH-:23].[K+]>O1CCOCC1>[F:12][C:13]1[CH:14]=[C:15]([C:20]2[CH:21]=[C:3]([C:2]([OH:11])=[O:23])[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:1]=2)[CH:16]=[CH:17][C:18]=1[F:19]

Komponenten

5

Edukt 3

HCID 7054IsatinHCID 14797Potassium HydroxideHCID 1230521-(3,4-Difluorophenyl)ethan-1-one

Produkt 1

HCID 46116332-(3,4-Difluorophenyl)-4-quinolinecarboxylic acidAusbeute 5,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 2,3-indolinedione (5 g, 0.03 mole), 3′,4′-difluoroacetophenone (5 g, 0.03 mole) and potassium hydroxide (3 g, 0.05 mole) in 1,4-dioxane (50 mL) is heated at 105° C. for 48 hours. The reaction solution is then cooled to room temperature and concentrated under reduced pressure. The residue is treated with EtOAc and extracted with water. The pH of the aqueous layer is adjusted to 5-6 with 1N HCl, the resulting solid is collected by vacuum filtration, washed with water, and dried to give the titled compound (450 mg) as a yellow solid.

Aufarbeitung

  1. temperatureThe reaction solution is then cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is treated with EtOAc
  4. extractionextracted with water
  5. filtrationthe resulting solid is collected by vacuum filtration
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ba1a3861c38f4b82a8002ce411707de2
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559163B2

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