Cinnamoylbenzene → 4,6-Diphenyl-2-pyridone

HRID 2380326

Reaktionsgleichung

Reaktionsgleichung von HRID 2380326
[CH:1](=[CH:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[C:18]([CH2:21][N+]1C=CC=CC=1)(=[O:20])[NH2:19].[OH-].[Na+]>CO.O>[C:11]1([C:9]2[CH:8]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[NH:19][C:18](=[O:20])[CH:21]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 7189CinnamoylbenzeneHCID 14798Sodium HydroxideHCID 27564401-(Carbamoylmethyl)pyridinium Chloride

Produkt 1

HCID 38462014,6-Diphenyl-2-pyridone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of benzylideneacetophenone (41.6 g) and N-carbamoylmethylpyridinium chloride (34.4 g) (prepared according to the method of O. ALBRECHT et al., Helv. Chim. Acta 24, 241E (1941)) in methanol (600 cc), is added, at room temperature, a 1N aqueous solution of sodium hydroxide (200 cc). The initially yellow solution takes on an orange colour and a yellow solid precipitates. The mixture is stirred at room temperature for 15 minutes and acetic acid (400 cc) is then added. The green solution obtained is stirred for 1 hour at room temperature. The solvent is then distilled in 4 hours under atmospheric pressure. The solid residue obtained is taken up in distilled water (500 cc). After stirring for 1 hour at more temperature, the solid is separated by filtration, washed with distilled water (3×100 cc) and dried under reduced pressure at 60° C. (whitish solid; m.p.=209°-212° C.)

Aufarbeitung

  1. customa yellow solid precipitates
  2. additionacetic acid (400 cc) is then added
  3. customThe green solution obtained
  4. stirringis stirred for 1 hour at room temperature
  5. distillationThe solvent is then distilled in 4 hours under atmospheric pressure
  6. customThe solid residue obtained
  7. stirringAfter stirring for 1 hour at more temperature
  8. customthe solid is separated by filtration
  9. washwashed with distilled water (3×100 cc)
  10. customdried under reduced pressure at 60° C. (whitish solid; m.p.=209°-212° C.)

Quellen und Nachweise

ORD-Eintrag
ord-5319b62429fc474e93ef5a19e3e0c3bd
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05366982

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