Water → 8-(2,6-Difluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid

HRID 43114

Reaktionsgleichung

Reaktionsgleichung von HRID 43114
[OH-:1].[K+].[F:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([O:12][CH3:13])=[C:6]([F:14])[C:5]=1[C:15]1[C:24]2[N:23]=[CH:22][CH:21]=[N:20][C:19]=2[C:18]([C:25]#N)=[CH:17][CH:16]=1.[OH2:27]>C(O)CO.CCOCC.O>[F:14][C:6]1[C:7]([O:12][CH3:13])=[CH:8][C:9]([O:10][CH3:11])=[C:4]([F:3])[C:5]=1[C:15]1[C:24]2[N:23]=[CH:22][CH:21]=[N:20][C:19]=2[C:18]([C:25]([OH:27])=[O:1])=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 592928748-(2,6-Difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonitrile

Produkt 1

HCID 592928348-(2,6-Difluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 174Ethylene GlycolLösungsmittelHCID 21584184Diethylether waterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A solution of KOH (2.4 g, 42.8 mmol, 10 equiv) in H2O (10 mL) was added to 8-(2,6-difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonitrile (Step 88.2) (1.4 g mg, 4.3 mmol) in ethylene glycol (20 mL). The reaction mixture was stirred at 150° C. for 4 h, allowed to cool to rt, diluted with Et2O/H2O, and extracted with Et2O. The aqueous phase was acidified to pH 5 by addition of 6 N HCl. Vacuum filtration of the resulting suspension afforded 1.47 g of the title compound as a brown solid, which was used without further purification: ESI-MS: 347.1 [M+H]+; tR=4.22 min (System 1).

Aufarbeitung

  1. temperatureto cool to rt
  2. extractionextracted with Et2O
  3. additionThe aqueous phase was acidified to pH 5 by addition of 6 N HCl
  4. filtrationVacuum filtration of the resulting suspension

Quellen und Nachweise

ORD-Eintrag
ord-a5a8986a6b90407f9491745da542121e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536175B2

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