Ethyl 7-[2(acetamidomethyl)-4-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate → 1-Ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 622495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 622495
C(NCC1SC=C([C:11]2[CH:20]=[C:19]3[C:14]([C:15](=[O:28])[C:16]([C:23]([O:25]CC)=[O:24])=[CH:17][N:18]3[CH2:21][CH3:22])=[CH:13][C:12]=2[F:29])N=1)(=O)C>Cl>[CH2:21]([N:18]1[C:19]2[C:14](=[CH:13][C:12]([F:29])=[CH:11][CH:20]=2)[C:15](=[O:28])[C:16]([C:23]([OH:25])=[O:24])=[CH:17]1)[CH3:22]

Komponenten

3

Edukt 1

HCID 13772764Ethyl 7-[2(acetamidomethyl)-4-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Produkt 1

HCID 107048941-Ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A solution of 0.32 g (0.76 mmol) ethyl 7-[2-(acetamidomethyl)-4-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 3 ml 6N hydrochloric acid was stirred at reflux three hours. The mixture was evaporated to dryness and the resulting solid was suspended in 5 ml water and dissolved by addition of 1N sodium hydroxide to pH 11. After filtration the product was precipitated by addition of 1N hydrochloric acid to pH 6.2, filtered, washed with water and dried to afford 0.22 g 7-[2-aminomethyl)-4-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 249°-254° C. (dec).

Aufarbeitung

  1. temperatureat reflux three hours
  2. customThe mixture was evaporated to dryness
  3. dissolutiondissolved by addition of 1N sodium hydroxide to pH 11
  4. filtrationAfter filtration the product
  5. customwas precipitated by addition of 1N hydrochloric acid to pH 6.2
  6. filtrationfiltered
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-410c6350e5124a088b844ddc97796ccd
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04771054

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