Reaktion #63204

Reaktionsgleichung

3-(3-Methyl-5-nitropyrid-2-yl)-3,3-bis(carbethoxy)propionitrile

sodium hydroxide

hydrochloric acid

→

title compound

Ausbeute 61.4%

5-Nitro-2-(2-cyanoethyl)-3-methylpyridine

Ausbeute 61.4%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was cooled from 28° C. to room temperature
2. 2
   workup.STIRRINGthe reaction was stirred for 2.75 hr
3. 3
   Temperatur, the pH was then raised to 7
4. 4
   workup.DISTILLATIONthe methanol was distilled off
5. 5
   ExtraktionThe aqueous phase was extracted with chloroform, extracts
6. 6
   Sonstigewere dried
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe residue was crystallised from chloroform/petroleum ether 40°-60° C
10. 10
    workup.ADDITIONThe crude product was treated with charcoal in ethanol
11. 11
    Sonstigerecrystallised from ethanol

Vorschrift

3-(3-Methyl-5-nitropyrid-2-yl)-3,3-bis(carbethoxy)propionitrile (29.8 g) was dissolved in methanol (1120 ml), molar sodium hydroxide solution (355 ml) was added, the reaction was cooled from 28° C. to room temperature and stirred for 55 minutes. The pH was lowered to 4 by the addition of concentrated hydrochloric acid, the reaction was stirred for 2.75 hr., the pH was then raised to 7 and the methanol was distilled off. The aqueous phase was extracted with chloroform, extracts were dried, filtered and concentrated. The residue was crystallised from chloroform/petroleum ether 40°-60° C. The crude product was treated with charcoal in ethanol and recrystallised from ethanol to give the title compound 10.44 g, m.p. 73°-74° C.

Quelle