Pyridine → 6-Phenyl-2-pyridone

HRID 613220

Reaktionsgleichung

Reaktionsgleichung von HRID 613220
ClCC([O:5][CH2:6][CH3:7])=O.[N:8]1C=CC=CC=1.Cl.CN(C)[CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O.C([O-])(=O)C.[NH4+]>C(O)C>[C:21]1([C:19]2[NH:8][C:6](=[O:5])[CH:7]=[CH:17][CH:18]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 7751Ethyl chloroacetateHCID 928441-Propanone, 3-(dimethylamino)-1-phenyl-, hydrochloride (1:1)HCID 517165Ammonium Acetate

Produkt 1

HCID 878896-Phenyl-2-pyridone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 2-chloroacetate (10.6 ml, 0.1 mol) is slowly added to hot (105° C.) pyridine (8.9 ml, 0.11 mol whereby the temperature is maintained in the range of 100° C. to 110° C. The resulting brown oil is dissolved in ethanol (60 ml), β-dimethylamino propiophenone hydrochloride (17.7 g, 0.1 mol; prepared according to Example 1) and ammonium acetate (60 g) are added and the mixture is boiled under reflux for 4 h. After cooling, the mixture is filtered and the solvent is evaporated in vacuo. The residue is crystallized from water, collected by filtration and purified by re-crystallization from toluene. The title compound is obtained as colorless crystals (4.7 g, 28% of th.) with mp. 200° C.

Aufarbeitung

  1. temperatureis maintained in the range of 100° C. to 110° C
  2. temperatureunder reflux for 4 h
  3. temperatureAfter cooling
  4. filtrationthe mixture is filtered
  5. customthe solvent is evaporated in vacuo
  6. customThe residue is crystallized from water
  7. filtrationcollected by filtration
  8. custompurified by re-crystallization from toluene

Quellen und Nachweise

ORD-Eintrag
ord-e8da0674e3194f368a28a8a48700cacb
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008161

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