Ethanol → 1-Cyclopropyl-6,8-difluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1651382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1651382
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:15]4[CH2:18][CH:17]([OH:19])[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:21])[C:6]([C:22]([O:24]CC)=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.C(O)C.[OH-].[Na+]>O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:15]4[CH2:16][CH:17]([OH:19])[CH2:18]4)[C:12]=3[F:14])[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 15615453Ethyl 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Produkt 1

HCID 104496511-Cyclopropyl-6,8-difluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 0.4 g (1.10 mmoles) of ethyl 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 2 ml of ethanol and 10 ml of 0.5N sodium hydroxide is left to reflux for 1.5 hours. It is then allowed to cool, diluted with water, adjusted to pH 5 and a precipitate is obtained which is filtered and washed with water. The solid is dried under vacuum yielding 0.37 g (100%) of 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid melting at 286°-288° C.

Aufarbeitung

  1. temperatureto reflux for 1.5 hours
  2. temperatureto cool
  3. customa precipitate is obtained which
  4. filtrationis filtered
  5. washwashed with water
  6. customThe solid is dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-289aede7b3354223bfcb6ea302f47c61
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04927926

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