1,3-Diethyl 2-oxopropanedioate → Ethyl 5-chloro-2-oxo-1,2-dihydroquinoxaline-3-carboxylate

HRID 240354

Reaktionsgleichung

Reaktionsgleichung von HRID 240354
[Cl:1][C:2]1[C:3]([NH2:9])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.O=[C:11]([C:17](OCC)=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[N:9]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17](=[O:18])[NH:8]2

Komponenten

4

Edukt 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 3462489(2-Amino-3-chlorophenyl)amine

Produkt 1

HCID 67531483Ethyl 5-chloro-2-oxo-1,2-dihydroquinoxaline-3-carboxylateAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

10.5 g (73.6 mmol) of 3-chloro-1,2-phenylenediamine and 12.8 g (73.5 mmol) of diethyl ketomalonate were dissolved in ethanol, and the solution was heated to reflux for 3 hours. While heating to reflux, ethanol was added thereto until precipitated crystals dissolved. The reaction mixture was cooled to room temperature, and then precipitated crystals were separated by filtration. The filter cake was washed with cold ethanol, and then dried, to obtain 10.5 g (yield: 51%) of ethyl 5-chloro-2-oxo-1,2-dihydroquinoxaline-3-carboxylate as pale yellow acicular crystals.

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureto reflux for 3 hours
  3. temperatureWhile heating
  4. temperatureto reflux
  5. customuntil precipitated crystals
  6. dissolutiondissolved
  7. customprecipitated crystals
  8. customwere separated by filtration
  9. washThe filter cake was washed with cold ethanol
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-06d5eda75c2e4224b9590b1360ec3dbe
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648075B2

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