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Acetic Acid → 5-amino-6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1458007
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1458007
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([CH3:14])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([O:21]CC)=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@@H:16]1[F:18].C(O)(=O)C.Cl>O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([CH3:14])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@@H:16]1[F:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 11759598Ethyl 5-amino-6,7-difluoro-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate

Produkt 1

HCID 110233625-amino-6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acidAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

A 10.43 g (30.6 mmol) portion of ethyl 5-amino-6,7-difluoro-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate was mixed with 150 ml of acetic acid and 150 ml of concentrated hydrochloric acid and then heated under reflux for 1 hour. After completion of the reaction, the reaction solution was spontaneously cooled and mixed with 700 ml of water. The thus formed crystals were collected by filtration, washed with water (100 ml×2), ethanol (300 ml×1) and ether (300 ml×1) in that order and then dried to yield 7.52 g (79%) of the title compound.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. customAfter completion of the reaction
  4. temperaturethe reaction solution was spontaneously cooled
  5. filtrationThe thus formed crystals were collected by filtration
  6. washwashed with water (100 ml×2), ethanol (300 ml×1) and ether (300 ml×1) in that order
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2d795fe8efbf4ddb88450310da64d819
Quelldatensatz
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05849757

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