Triethyl Phosphate → Ethyl 1-ethyl-5-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 525935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525935
[F:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:6][NH:7]2.F[C:23]1C=C2C(C(=O)C(C(OCC)=O)=CN2)=C(OC)[C:24]=1OC.C(=O)([O-])[O-].[K+].[K+].P(OCC)(OCC)(OCC)=O>O>[CH2:23]([N:7]1[C:8]2[C:3](=[C:2]([F:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=2)[C:4](=[O:21])[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:6]1)[CH3:24]

Komponenten

6

Edukt 4

HCID 6535Triethyl PhosphateHCID 11430Potassium CarbonateHCID 86732801Ethyl 7-fluoro-5,6-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylateHCID 86732802Ethyl 5-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

Produkt 1

HCID 86732803Ethyl 1-ethyl-5-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylateAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of ethyl 5-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate and ethyl 7-fluoro-5,6-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (103 g, 349 mmol), and potassium carbonate (72.3 g, 523 mmol) in triethyl phosphate (297 ml, 1744 mmol) was stirred at 120° C. for 8 h. LCMS indicated completion of the reaction. The reaction mixture was cooled down to rt and diluted with water, extracted with DCM, dried over sodium sulfate and concentrated in vacuo. The crude material was recrystallized in EtOH, the precipitate was collected by filtration and washed by cold EtOH and dried in air. Another recrystallization afforded pure ethyl 1-ethyl-5-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (65 g, 201 mmol, 57.6% yield) as a brown solid. LCMS: (M+H)+: 324.1.

Aufarbeitung

  1. customcompletion of the reaction
  2. temperatureThe reaction mixture was cooled down to rt
  3. extractionextracted with DCM
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude material was recrystallized in EtOH
  7. filtrationthe precipitate was collected by filtration
  8. washwashed by cold EtOH
  9. customdried in air
  10. customAnother recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-a0e1ef3c75644de480d9b9e5db872a98
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340556B2

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