Cyanuric chloride → 7-FLUORO-6-METHOXY-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBONITRILE

HRID 1837328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837328
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12]([NH2:14])=O)=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:16][CH3:17].N1C(Cl)=NC(Cl)=NC=1Cl.C(=O)(O)[O-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12]#[N:14])=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:16][CH3:17]

Komponenten

5

Edukt 3

HCID 7954Cyanuric chloride2×HCID 516892Sodium BicarbonateHCID 121507017-Fluoro-1,4-dihydro-6-methoxy-4-oxo-3-quinolinecarboxamide

Produkt 1

HCID 121507027-FLUORO-6-METHOXY-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBONITRILEAusbeute 41,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 7-fluoro-6-methoxy-4-oxo-1,4,-dihydro-3-quinolinecarboxamide (700 mg, 3.0 mmol) and cyanuric chloride (341 mg, 1.65 mmol) in 15 mL of N,N,-dimethylformamide is heated at 65° C. for 6 hours then cooled to room temperature and an additional 206 mg of cyanuric chloride is added. The mixture is heated at 65° C. for 4 hours then stirred overnight at room temperature. The reaction mixture is poured into ice water and neutralized with saturated sodium bicarbonate. The solids are collected by filtration washing with water and hexane to provide 610 mg of crude product. Purification by flash column chromatography eluting with a gradient of 3% methanol in dichloromethane to 10% methanol in dichloromethane, provides 272 mg of 7-fluoro-6-methoxy-4-oxo-1,4-dihydro-3-quinolinecarbonitrile, mp 147-149° C.

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. temperatureThe mixture is heated at 65° C. for 4 hours
  3. filtrationThe solids are collected by filtration
  4. washwashing with water and hexane
  5. customto provide 610 mg of crude product
  6. customPurification by flash column chromatography
  7. washeluting with a gradient of 3% methanol in dichloromethane to 10% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-3c1bad142b3c4e9794358d566fb1eef7
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06780996B2

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