Phenylglyoxylic Acid → 1-(2,2-difluoroethyl)-3-phenyl-quinoxalin-2(1H)-one

HRID 1961559

Reaktionsgleichung

Reaktionsgleichung von HRID 1961559
[F:1][CH:2]([F:12])[CH2:3][NH:4][C:5]1[C:6]([NH2:11])=[CH:7][CH:8]=[CH:9][CH:10]=1.O=[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:15](O)=[O:16]>CO>[F:1][CH:2]([F:12])[CH2:3][N:4]1[C:5]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:11]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]1=[O:16]

Komponenten

4

Edukt 2

HCID 11915Phenylglyoxylic AcidHCID 58110951N-(2,2-difiuoroethyl)benzene-1,2-diamine

Produkt 1

HCID 442244821-(2,2-difluoroethyl)-3-phenyl-quinoxalin-2(1H)-oneAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 400 mg (2,32 mM) of N-(2,2-difluoroethyl)benzene-1,2-diamine in 7 ml of methanol were added 349 mg (2,32 mM) of 2-Oxo-2-phenylacetic acid. The mixture was refluxed for 3 h and the solvent was then removed under vacuum. The residue was further purified by silica gel column chromatography using dichloromethane/cyclohexane as eluant, to give 231,8 mg of 1-(2,2-difluoroethyl)-3-phenyl-quinoxalin-2(1H)-one as a pale beige solid. Yield: 35%.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 h
  2. customthe solvent was then removed under vacuum
  3. customThe residue was further purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-70d6de29aa0d4ab79def173aa43d4a16
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415352B2

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