Methyl iodide → Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 4558

Reaktionsgleichung

Reaktionsgleichung von HRID 4558
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]=[CH:7][C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]2[OH:22].[C:23](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]([CH3:23])[CH:7]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178418515HCID 178418515, Verbindung

Produkt 1

HCID 13670061Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylateAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 1.5 g (0.005 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-carboxylate and 1.4 g (0.01 mol) of potassium carbonate in 10 ml of dimethylformamide is heated for 30 minutes at 60° C. and left to cool, 2.15 g (3×0.005 mol) of methyl iodide are added, the mixture is heated at 80°-90° C. for 4 hours and left to cool, 25 ml of a water/ice mixture are added and the precipitate formed is filtered off and washed with water. The precipitate is receystallized from ethanol to give 1.2 g of a solid melting at 253°-254° C.

Aufarbeitung

  1. waitleft
  2. temperatureto cool
  3. temperaturethe mixture is heated at 80°-90° C. for 4 hours
  4. waitleft
  5. temperatureto cool
  6. customthe precipitate formed
  7. filtrationis filtered off
  8. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-56876a15c54c4de4818fa1eeae7b7038
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727080

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