2-(Phenylamino)benzonitrile → Ethyl 4-amino-2-oxo-1-phenyl-1,2-dihydro-quinoline-3-carboxylate

HRID 377619

Reaktionsgleichung

Reaktionsgleichung von HRID 377619
[O-]CC.[Na+].C(O)C.[Na].[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][C:11]([O-:13])=O.[C:18]1([NH:24][C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[C:27]#[N:28])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[NH2:28][C:27]1[C:26]2[C:25](=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11](=[O:13])[C:10]=1[C:9]([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

6

Edukt 4

HCID 2528802-(Phenylamino)benzonitrileHCID 3595298Propanedioic acid, monoethyl esterHCID 5360545SodiumHCID 23706232Ethanol sodium ethoxide

Produkt 1

HCID 19356221Ethyl 4-amino-2-oxo-1-phenyl-1,2-dihydro-quinoline-3-carboxylateAusbeute 51,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Into a sodium ethoxide/ethanol solution which had been prepared from 2.07 g (90 mmol) of metallic sodium and 75 ml of anhydrous ethanol, 14.4 g (90 mmol) of ethyl malonate were added dropwise at room temperature. After the resultant mixture was stirred for 30 minutes as was, 5.82 g (30 mmol) of 2-phenylaminobenzonitrile were added and the mixture so obtained was heated under reflux for 48 hours. The reaction mixture was concentrated under reduced pressure, followed by the addition of ethyl acetate. The resulting solution was washed with water and was then dried. The solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column and was then recrystallized from chloroform/hexane, whereby 4.78 g of ethyl 4-amino-2-oxo-1-phenyl-1,2-dihydro-quinoline-3-carboxylate (Compound No. 1) were obtained (yield: 51.7%).

Aufarbeitung

  1. additionwere added dropwise at room temperature
  2. customthe mixture so obtained
  3. temperaturewas heated
  4. temperatureunder reflux for 48 hours
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. additionfollowed by the addition of ethyl acetate
  7. washThe resulting solution was washed with water
  8. customwas then dried
  9. distillationThe solvent was distilled off under reduced pressure
  10. customThe residue was purified by chromatography on a silica gel column
  11. customwas then recrystallized from chloroform/hexane

Quellen und Nachweise

ORD-Eintrag
ord-032e1a16f50b49e68f874f7e59ca4e90
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028081

Verknüpfte Notizen

Wird geladen…