Piperidine → 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone

HRID 38305

Reaktionsgleichung

Reaktionsgleichung von HRID 38305
[C:1]([C:4]1[C:5](=[O:12])[NH:6][C:7]([CH3:11])=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:2].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=O.N1CCCCC1>N1C=CC=CC=1.O>[OH:10][C:9]1[CH:8]=[C:7]([CH3:11])[NH:6][C:5](=[O:12])[C:4]=1[C:1](=[O:3])[CH:2]=[CH:17][C:16]1[CH:19]=[CH:20][C:21]([O:22][C:23]([F:24])([F:25])[F:26])=[C:14]([Cl:13])[CH:15]=1

Komponenten

6

Edukt 3

HCID 8082PiperidineHCID 27788913-Chloro-4-(trifluoromethoxy)benzaldehydeHCID 546761542(1H)-Pyridinone, 3-acetyl-4-hydroxy-6-methyl-

Produkt 1

HCID 1363673444-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinoneAusbeute 36,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 0.50 g of 3-acetyl-4-hydroxy-6-methyl-2(1H)-pyridinone, 0.74 g of 3-chloro-4-(trifluoromethoxy)benzaldehyde, 6 mg of pyridine and 0.1 ml of piperidine was heated under refluxing for 4 hours. After cooled to room temperature, 40 ml of water was added to the reaction mixture, precipitated crystals were filtered, and this was washed with tetrahydrofuran, then with ethyl acetate to obtain 0.41 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone [Compound No. (3a-32)] as a yellow crystal.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder refluxing for 4 hours
  3. customprecipitated crystals
  4. filtrationwere filtered
  5. washthis was washed with tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-92d980da2a324de2b436ae444770958c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524729B2

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