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Hydrochloric Acid → 7-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 600859
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 600859
[F:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([O:19]CC)=[O:18])=[CH:8][N:9]2[C@@H:13]2[CH2:15][C@@H:14]2[F:16])=[CH:4][CH:3]=1.Cl>C(O)(=O)C>[F:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([OH:19])=[O:18])=[CH:8][N:9]2[C@@H:13]2[CH2:15][C@@H:14]2[F:16])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 67271688Ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate

Produkt 1

HCID 577586807-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate (1.40 g, 4.56 mmol) was dissolved in acetic acid (4 ml), and after adding concentrated hydrochloric acid (4 ml) thereto, it was heated under reflux for 3 hours. After cooling, the reaction solution was poured into ice water (50 ml) and the precipitated crystals were filtered out. After washing the filtered-out crystals with an excess amount of water, washing in cold ethanol and washing in diethyl ether were performed in that order, and after drying under a reduced pressure, 1.18 g (93%) of the title compound was obtained in the form of a white powder.

Aufarbeitung

  1. temperatureit was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals were filtered out
  5. washAfter washing the filtered-out crystals with an excess amount of water
  6. washwashing in cold ethanol
  7. washwashing in diethyl ether
  8. customafter drying under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-597121bfda5c4cbda520ef4b3f4906bc
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07902226B2

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