Phenylacetonitrile → beta-Oxo-alpha-phenyl-3-pyridinepropanenitrile

HRID 1167645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1167645
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:12]1([CH2:18][C:19]#[N:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C.O>[C:19]([CH:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:9])#[N:20]

Komponenten

6

Edukt 3

HCID 8794PhenylacetonitrileHCID 69188Ethyl NicotinateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 3765543beta-Oxo-alpha-phenyl-3-pyridinepropanenitrileAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of ethyl nicotinate (10 g) and phenylacetonitrile (5.1 g) in tert-butyl alcohol (30 mL), was added potassium tert-butoxide (6.4 g), and the mixture was stirred at 100° C. for 3 h. After cooling, the resulting mixture was dissolved in water and washed with isopropyl ether. The aqueous phase was adjusted to pH 7.0 with 2 N hydrochloric acid and extracted with ethyl acetate. The extracts were washed with water, dried, and the solvent was evaporated. The crystalline residue was recrystallized from ethyl acetate-isopropyl ether to obtain the title compound (6.0 g, yield 62%).

Aufarbeitung

  1. temperatureAfter cooling
  2. washwashed with isopropyl ether
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water
  5. customdried
  6. customthe solvent was evaporated
  7. customThe crystalline residue was recrystallized from ethyl acetate-isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ce1f39d40dc6494e99758909089d0bc2
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620825B1

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