Sodium Hydroxide → 5-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acid

HRID 561154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561154
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([C:25]([O:27]CC)=[O:26])=[C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[N:7]2[CH:16]1[CH2:18][CH2:17]1.[OH-].[Na+]>CCO>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([C:25]([OH:27])=[O:26])=[C:6]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[N:7]2[CH:16]1[CH2:17][CH2:18]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 59002984Ethyl 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate

Produkt 1

HCID 590030445-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acidAusbeute 62.953.556 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylate (980 mg, 2.36 nmol) and 1M aq. NaOH (5 mL) in EtOH (15 mL) was stirred at 50° C. for 24 h. After the reaction mixture was concentrated in vacuo, the residue was dissolved in water and 2M HCl was added to pH<3. The crude product was extracted with EtOAc, washed with brine, dried over MgSO4 and the solvent was removed in vacuo. The crude product was purified by column chromatography (Hexane:EtOAc 5:1→1:1) to yield 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acid (574 mg, 63%) as a yellow amorphous solid.

Aufarbeitung

  1. concentrationAfter the reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. addition2M HCl was added to pH<3
  4. extractionThe crude product was extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed in vacuo
  8. customThe crude product was purified by column chromatography (Hexane:EtOAc 5:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-da13fc96bdc147d3b447094618053b06
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063221B2

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