Sodium Hydroxide → 1-Cyclopropyl-6-fluoro-7-chloro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1288

Reaktionsgleichung

Reaktionsgleichung von HRID 1288
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:16])[C:10]([F:15])=[C:11](Br)[CH:12]=3)[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.S(Cl)([Cl:23])=O.[OH-].[Na+]>>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:16])[C:10]([F:15])=[C:11]([Cl:23])[CH:12]=3)[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1

Komponenten

4

Edukt 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 101320157-Bromo-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Produkt 1

HCID 146512841-Cyclopropyl-6-fluoro-7-chloro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Versuchsvorschrift

To 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4- dihydro-4-oxoquinoline-3-carboxylic acid (0.2 g) is added thionyl chloride (2 ml) and the mixture is refluxed for 1 hour. After cooling, the reaction mixture is poured into ice-water and made alkaline with 10% aqueous sodium hydroxide solution. After stirring for 30 minutes, the resultant is extracted with dichloromethane. The aqueous layer is made acidic with 10% hydrochloric acid and then extracted with dichloroethane. The solvent is concentrated and the residue is recrystallized from acetic acid to give 1-cyclopropyl-6-fluoro-7-chloro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (80 mg), as white crystals, m.p. 258°-260° C.

Aufarbeitung

  1. temperaturethe mixture is refluxed for 1 hour
  2. temperatureAfter cooling
  3. extractionthe resultant is extracted with dichloromethane
  4. extractionextracted with dichloroethane
  5. concentrationThe solvent is concentrated
  6. customthe residue is recrystallized from acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-f9699d46336a408a989760bcba92ed2e
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723648

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