3-Fluoroaniline → Ethyl 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 393941

Reaktionsgleichung

Reaktionsgleichung von HRID 393941
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C([O:11][CH2:12][CH:13]([C:19](OCC)=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:6]([C:12]([OH:11])=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:19]=[N:5]2)=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 97423-FluoroanilineHCID 98702Diethyl (ethoxymethyl)malonate

Produkt 1

HCID 178469609Ethyl 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateAusbeute 67,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under a nitrogen atmosphere, 3-fluoroaniline (50.0 g, 0.45 mol) and diethyl ethoxymethylmalonate (91 mL, 0.45 mol) were combined and heated at 100° C. for 3 hours. The reaction was allowed to cool to ambient temperature and it solidified. Dowtherm A (200 mL) was added and the reaction mixture was heated at 240° C. for 4 hours. The reaction mixture was allowed to cool to ambient temperature. The resulting precipitate was isolated by filtration, washed with hexane and then dried in a vacuum oven to provide 71.5 g of ethyl 7-fluoro-4-hydroxy-3-quinolinecarboxylate.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. temperaturethe reaction mixture was heated at 240° C. for 4 hours
  3. temperatureto cool to ambient temperature
  4. customThe resulting precipitate was isolated by filtration
  5. washwashed with hexane
  6. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-634289ea48ee4766bd160165ae5e52f6
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809203B2

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