Ethanol → Ethyl isonicotinimidate

HRID 1995902

Reaktionsgleichung

Reaktionsgleichung von HRID 1995902
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)#[N:2].[CH2:9]([OH:11])[CH3:10]>C(Cl)(Cl)Cl>[C:1](=[NH:2])([O:11][CH2:9][CH3:10])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 702EthanolHCID 75064-Cyanopyridine

Produkt 1

HCID 12263946Ethyl isonicotinimidate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 4-cyanopyridine (135 g) and ethanol (83.3 ml) in chloroform (1000 ml) is cooled in an ice bath for 30 min. Anhydrous HCl (143 g) is bubbled into the cold mixture over a period of 7 hours with stirring continued overnight with cooling. The reaction mixture is filtered and the filtered solid added portionwise to an ice cold 10% K2CO3 solution (500 g in 5 l H2O) with stirring. A liter of ether is added to the mixture after 20 min with stirring. The aqueous layer is extracted with ether and the organic extracts combined and dried overnight. The dried solution is filtered, evaporated in vacuo and vacuum distilled giving as a main fraction 75.5 g of a colorless liquid, b.p. 63°-65° C. (0.14 mm).

Aufarbeitung

  1. customAnhydrous HCl (143 g) is bubbled into the cold mixture over a period of 7 hours
  2. temperaturewith cooling
  3. filtrationThe reaction mixture is filtered
  4. additionthe filtered solid added portionwise to an ice cold 10% K2CO3 solution (500 g in 5 l H2O)
  5. stirringwith stirring
  6. additionA liter of ether is added to the mixture after 20 min
  7. stirringwith stirring
  8. extractionThe aqueous layer is extracted with ether
  9. customdried overnight
  10. filtrationThe dried solution is filtered
  11. customevaporated in vacuo and vacuum
  12. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-8921c61f550549e6be0a74ff1b0f2041
Quelldatensatz
uspto-grants-1983_09
Patentnummer
US04406897

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