4-Chloroaniline → methyl 6-chloro-4-oxo-1,4-dihydroquinoline-2-carboxylate

HRID 902876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902876
[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3](OC)=[O:4].[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>CO>[Cl:11][C:12]1[CH:13]=[C:14]2[C:15](=[CH:17][CH:18]=1)[NH:16][C:1]([C:7]([O:9][CH3:10])=[O:8])=[CH:2][C:3]2=[O:4]

Komponenten

4

Edukt 2

HCID 78124-ChloroanilineHCID 12980Dimethyl acetylenedicarboxylate

Produkt 1

HCID 5200373methyl 6-chloro-4-oxo-1,4-dihydroquinoline-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
240 °C

Versuchsvorschrift

Dimethyl acetylenedicarboxylate (13.5 ml) was added to a solution of 4-chloroaniline (12.76 g) in methanol (150 ml), and the mixture was heated under reflux for 8 hours. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in diphenyl ether (70 ml), and the solution was heated under reflux at 240° C. for 4 hours. After cooling the reaction mixture, a mixed solvent of hexane and diethyl ether was added, and crystals deposited were collected by filtration and washed to obtain the title compound (11.09 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in diphenyl ether (70 ml)
  5. temperaturethe solution was heated
  6. temperatureAfter cooling the reaction mixture
  7. additiona mixed solvent of hexane and diethyl ether was added
  8. filtrationcrystals deposited were collected by filtration
  9. washwashed

Quellen und Nachweise

ORD-Eintrag
ord-9d2bc446a18449daa2d9e34b5287be5d
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365205B2

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