Potassium Carbonate → Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-cyclopropylmethyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 4562

Reaktionsgleichung

Reaktionsgleichung von HRID 4562
[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(=O)([O-])[O-].[K+].[K+].[CH:29]1([CH2:32]Br)[CH2:31][CH2:30]1>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]([CH2:32][CH:29]1[CH2:31][CH2:30]1)[CH:7]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 178418515HCID 178418515, Verbindung

Produkt 1

HCID 13670064Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-cyclopropylmethyl-4-oxo-1,4-dihydroquinoline-3-carboxylateAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3.6 g (0.012 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-carboxylate and 4.15 g (0.03 mol) of potassium carbonate in 30 ml of dimethlformamide is heated for 30 minutes at 80° C. and left to cool, 8 g (0.06 mol) of cyclopropylmethyl bromide are added, the mixture is kept for 12 hours at 90° C. and left to cool, 80 ml of a water/ice mixture are added and the precipitate formed is filtered off, washed with water and recrystallized from ethanol to give 2.65 g of a solid melting at 125°-127° C.

Aufarbeitung

  1. waitleft
  2. temperatureto cool
  3. waitleft
  4. temperatureto cool
  5. customthe precipitate formed
  6. filtrationis filtered off
  7. washwashed with water
  8. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-fd0d21daeb32407586c452e4c390cba8
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727080

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