2-Methoxyethanol → 3-Quinolinecarbonitrile, 4-hydroxy-6-methoxy-7-(2-methoxyethoxy)-

HRID 1837331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837331
[Na].[CH3:2][O:3][CH2:4][CH2:5][OH:6].F[C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:20])[C:13]([C:18]#[N:19])=[CH:14][NH:15]2)=[CH:10][C:9]=1[O:21][CH3:22]>C(O)(=O)C>[CH3:22][O:21][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:8]=1[O:6][CH2:5][CH2:4][O:3][CH3:2])[NH:15][CH:14]=[C:13]([C:18]#[N:19])[C:12]2=[O:20]

Komponenten

5

Edukt 3

HCID 80192-MethoxyethanolHCID 5360545SodiumHCID 121507027-FLUORO-6-METHOXY-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBONITRILE

Produkt 1

HCID 99705583-Quinolinecarbonitrile, 4-hydroxy-6-methoxy-7-(2-methoxyethoxy)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Sodium (84 mg, 3.67 mmol) is added to 3.6 mL of 2-methoxyethanol and the mixture is heated at reflux for 90 minutes. 7-Fluoro-6-methoxy-4-oxo-1,4,-dihydro-3-quinolinecarbonitrile (200 mg, 0.92 mmol) is added and the reaction mixture is heated at reflux for 4 hours then stirred at room temperature overnight. The reaction mixture is poured into ice water and acidified with acetic acid. The solids are collected by filtration, washing with ethyl acetate and hexane, to provide 234 mg of 6-methoxy-7-(2-methoxyethoxy)-4-oxo-1,4,-dihydro-3-quinolinecarbonitrile, mp>300° C.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 90 minutes
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux for 4 hours
  5. filtrationThe solids are collected by filtration
  6. washwashing with ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-290ec1f075fa4aebb23c1a80664cbfa8
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06780996B2

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