Sodium Bicarbonate → 8-bromo-4-hydroxy-5-methoxy-3-Quinolinecarboxylic acid ethyl ester

HRID 401224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401224
C(O[C:4](=[O:22])[C:5](=[CH:11][NH:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[Br:21])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:9]([O:8][C:6]([C:5]1[C:4](=[O:22])[C:18]2[C:13](=[C:14]([Br:21])[CH:15]=[CH:16][C:17]=2[O:19][CH3:20])[NH:12][CH:11]=1)=[O:7])[CH3:10]

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 103846312-[(2-Bromo-5-methoxyphenylamino)methylene]malonic acid diethyl ester

Produkt 1

HCID 102458028-bromo-4-hydroxy-5-methoxy-3-Quinolinecarboxylic acid ethyl esterAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-[(2-Bromo-5-methoxy-phenylamino)-methylene]-malonic acid diethyl ester (9 g, 24.2 mmol) was slowly added to polyphosphoric acid (30 g) at 120° C. The mixture was stirred at this temperature for additional 30 min and then cooled to room temperature. Absolute ethanol (30 mL) was added and the resulting mixture was refluxed for 30 min. The mixture was basified with aqueous sodium bicarbonate at 25° C. and extracted with EtOAc (4×100 mL). The organic layers were combined, dried and the solvent evaporated to give 8-bromo-5-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (2.3 g, 30%).

Aufarbeitung

  1. temperaturethe resulting mixture was refluxed for 30 min
  2. extractionextracted with EtOAc (4×100 mL)
  3. customdried
  4. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-4aad2fca700547fdb63f3c727e54e2ae
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741925B2

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