2-Bromoethanol → Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 4560

Reaktionsgleichung

Reaktionsgleichung von HRID 4560
[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+].[CH2:29](Br)[CH2:30][OH:31]>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]([CH2:29][CH2:30][OH:31])[CH:7]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22]

Komponenten

5

Edukt 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 178418515HCID 178418515, Verbindung

Produkt 1

HCID 13670063Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylateAusbeute 45,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2 g (0.0076 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-caboxylate and 1.85 g (2×0.0076 mol) of potassium carbonate in 20 ml of dimethylformamide is heated for 30 minutes at 60° C. and left to cool, 3.35 g (4×0.0076 mol) of ethylene bromohydrin are added, the mixture is heated at 80°-90° C. for 10 hours, active carbon is added, the mixture is filtered hot, the filtrate is evaporated to dryness, water is added and the precipitate formed is filtered off and washed with water. It is recrystallized from dimethylformamide to give 1.2 g of a solid melting at 237°-239° C.

Aufarbeitung

  1. waitleft
  2. temperatureto cool
  3. temperaturethe mixture is heated at 80°-90° C. for 10 hours
  4. additionactive carbon is added
  5. filtrationthe mixture is filtered hot
  6. customthe filtrate is evaporated to dryness, water
  7. additionis added
  8. customthe precipitate formed
  9. filtrationis filtered off
  10. washwashed with water
  11. customIt is recrystallized from dimethylformamide

Quellen und Nachweise

ORD-Eintrag
ord-d71e37624aff4110a72e833bc5f49268
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727080

Verknüpfte Notizen

Wird geladen…