Water → Ethyl 6,7-difluoro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2247921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2247921
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([F:18])=[C:12]([F:17])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2].CI.[C:21](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([F:18])=[C:12]([F:17])[CH:13]=2)[N:8]([CH3:21])[CH:7]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 751784Ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-xynoline carbonate

Produkt 1

HCID 14423855Ethyl 6,7-difluoro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6,7-Difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester (10.0 g, 39.5 mmol), methyl iodide (56 g, 395 mmol) and potassium carbonate (10.9 g, 79 mmol) were combined in dimethylformamide and heated to 90° for 20 hours. The reaction mixture was cooled and poured into cold water (1.5 l). The precipitate was filtered, washed with cold water and recrystallized from ethyl acetate to yield the title product as white needles, m.p. 210°-212° (6.60 g, 24.7 mmol, 63% yield).

Aufarbeitung

  1. temperatureheated to 90° for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe precipitate was filtered
  4. washwashed with cold water
  5. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-18b7ea7aa6a24994ac5c2d7ed19090e5
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05037834

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