Potassium Carbonate → 1-(2-Fluoroethyl)-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 544218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544218
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([Cl:18])=[C:12]([F:17])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])C.C(=O)([O-])[O-].[K+].[K+].[F:25][CH2:26][CH2:27]I>CN(C=O)C>[Cl:18][C:11]1[CH:10]=[C:9]2[C:14]([C:15](=[O:16])[C:6]([C:4]([OH:3])=[O:5])=[CH:7][N:8]2[CH2:27][CH2:26][F:25])=[CH:13][C:12]=1[F:17]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 3018009Ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Produkt 1

HCID 127338801-(2-Fluoroethyl)-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred mixture of the above ester (1.35 g), potassium carbonate (1.73 g) and DMF (20 ml), 4.35 g of 2-fluoroethyl iodide was added and the mixture was stirred at 80° -90° C. for 9.5 hours. After the solvent evaporated off, the residue was extracted with dichromomethane, the dichloromethane layer was washed with water, and dried. The solvent was evaporated. The residue was added to 18% hydrochloric acid (20 ml) and refluxed for 3 hours. After the mixture cooled, the solid was filtered, washed with water, dried, and recrystallized from a mixture of DMF and ethanol to give 7-chloro-6-fluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.0 g).

Aufarbeitung

  1. additionwas added
  2. customAfter the solvent evaporated off
  3. extractionthe residue was extracted with dichromomethane
  4. washthe dichloromethane layer was washed with water
  5. customdried
  6. customThe solvent was evaporated
  7. additionThe residue was added to 18% hydrochloric acid (20 ml)
  8. temperaturerefluxed for 3 hours
  9. temperatureAfter the mixture cooled
  10. filtrationthe solid was filtered
  11. washwashed with water
  12. customdried
  13. customrecrystallized from a mixture of DMF and ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2d71c3c874bd4c1e8fd6b6cc210a9075
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04448962

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