Sodium Iodide → 1-(2-Fluoroethyl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 434565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 434565
C(=O)([O-])[O-].[K+].[K+].C([O:9][C:10]([C:12]1[C:21](=[O:22])[C:20]2[C:15](=[C:16]([F:25])[C:17]([F:24])=[C:18]([F:23])[CH:19]=2)[NH:14][CH:13]=1)=[O:11])C.Br[CH2:27][CH2:28][F:29].[I-].[Na+]>CN(C=O)C>[F:23][C:18]1[CH:19]=[C:20]2[C:15](=[C:16]([F:25])[C:17]=1[F:24])[N:14]([CH2:27][CH2:28][F:29])[CH:13]=[C:12]([C:10]([OH:9])=[O:11])[C:21]2=[O:22]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 27339723-Quinolinecarboxylic acid, 1,4-dihydro-4-oxo-6,7,8-trifluoro-, ethyl ester

Produkt 1

HCID 127709081-(2-Fluoroethyl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidAusbeute 39,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Anhydrous potassium carbonate (2.2 g), 6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester (0.8 g), 1-bromo-2-fluoroethane (3.8 g), sodium iodide (4.5 g), and DMF (30 ml) were combined and heated with stirring at 90°-100° C. for 10 hours. After the solvent evaporated and cooled, water was added to the residue and extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate, and evaporated. To the residual solid was added a mixture of 18% hydrochloric acid (14 ml) and ethanol (7 ml) and the acidic mixture was refluxed for 2.5 hours. Water (14 ml) and ethanol (14 ml) were added to the reaction mixture and cooled. The precipitate was collected by filtration and recrystallized from a mixture of DMF and ethanol to give 6,7,8-trifluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.34 g), mp 208°-210° C.

Aufarbeitung

  1. temperatureheated
  2. customAfter the solvent evaporated
  3. temperaturecooled
  4. additionwater was added to the residue
  5. extractionextracted with dichloromethane
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated
  9. additionTo the residual solid was added
  10. additiona mixture of 18% hydrochloric acid (14 ml) and ethanol (7 ml)
  11. temperaturethe acidic mixture was refluxed for 2.5 hours
  12. additionWater (14 ml) and ethanol (14 ml) were added to the reaction mixture
  13. temperaturecooled
  14. filtrationThe precipitate was collected by filtration
  15. customrecrystallized from a mixture of DMF and ethanol

Quellen und Nachweise

ORD-Eintrag
ord-d853e618d40448089a43efdae433b006
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04398029

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