Pyridine → 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone

HRID 38309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 38309
[C:1]([C:4]1[C:5](=[O:15])[NH:6][C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=O.N1C=CC=CC=1.N1CCCCC1>O>[OH:14][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5](=[O:15])[C:4]=1[C:1](=[O:3])[CH:2]=[CH:20][C:19]1[CH:22]=[CH:23][C:24]([O:25][C:26]([F:27])([F:28])[F:29])=[C:17]([Cl:16])[CH:18]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 8082PiperidineHCID 27788913-Chloro-4-(trifluoromethoxy)benzaldehydeHCID 546825123-Acetyl-2,4-dihydroxyquinoline

Produkt 1

HCID 695121564-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinoneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 0.60 g of 3-acetyl-4-hydroxy-2(1H)-quinolinone, 1.99 g of 3-chloro-4-(trifluoromethoxy)benzaldehyde, 10 ml of pyridine and 88 μl of piperidine was heated under refluxing overnight. After cooling to room temperature, 50 ml of water was added to the reaction mixture, and precipitated crystals were filtered, and washed with 40 ml of tetrahydrofuran, and 60 ml of hexane to obtain 0.92 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone [Compound No. (3c-32)] as a yellow crystal.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder refluxing overnight
  3. customprecipitated crystals
  4. filtrationwere filtered
  5. washwashed with 40 ml of tetrahydrofuran, and 60 ml of hexane

Quellen und Nachweise

ORD-Eintrag
ord-31190487ee7542c5af8bd15daeb36fda
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524729B2

Notizen zur Reaktion

Wird geladen…