Ammonium Carbonate → Ethyl 6-amino-1-cyclopropyl-7-fluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate

HRID 561156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561156
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:18]([O-:20])=[O:19])[C:10](F)=[C:11]([F:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[NH4+:31].[NH4+]>CN(C=O)C>[NH2:31][C:10]1[C:9]([N+:18]([O-:20])=[O:19])=[C:8]2[C:13](=[C:12]([O:14][CH3:15])[C:11]=1[F:16])[N:4]([CH:1]1[CH2:3][CH2:2]1)[CH:5]=[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:7]2=[O:21]

Komponenten

4

Edukt 2

HCID 517111Ammonium CarbonateHCID 10666701Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate

Produkt 1

HCID 59002951Ethyl 6-amino-1-cyclopropyl-7-fluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylateAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (5.00 g, 13.5 mmol) and ammonium carbonate (11.7 g, 122 mmol) in DMF (50 mL) was stirred at 90° C. for 18 h. After the reaction mixture was poured into ice-water, the crude product was extracted with CH2Cl2, washed with brine, dried over MgSO4 and the solvent was removed in vacuo. The crude product washed with EtOH and dried to yield ethyl 6-amino-1-cyclopropyl-7-fluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (2.55 g, 52%) as a yellow solid.

Aufarbeitung

  1. extractionthe crude product was extracted with CH2Cl2
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed in vacuo
  5. washThe crude product washed with EtOH
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-85f518514b554e1db6f8d527d3bec36a
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063221B2

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