Reacción #96231

Ecuación de reacción

2-isobutylaminonicotinonitrile

ethyl malonyl chloride

ethyl ether

→

title product

4-Amino-1-Isobutyl-1,2-Dihydro-2-Oxo-1,8-Naphthyridine-3-Carboxylic Acid Ethyl Ester

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónwas filtered
2. 2
   OtroThe filtrate was evaporated in a rotary evaporator
3. 3
   workup.DISSOLUTIONthe residue was dissolved in 20 ml
4. 4
   workup.ADDITIONThis solution was added to a solution of 1.6 g
5. 5
   workup.STIRRINGAfter stirring at room temperature for 5 minutes
6. 6
   workup.ADDITIONthe mixture was diluted with water
7. 7
   OtroThe precipitate which formed
8. 8
   Otrowas collected
9. 9
   Otroair dried
10. 10
    Otrowas recrystallized from ethyl acetate
11. 11
    Otroto afford 2.1 g

Procedimiento

To a solution of 12.25 g (0.07 mole) of 2-isobutylaminonicotinonitrile in 300 ml. of anhydrous ethyl ether was added 5.2 g. (0.035 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 30 minutes and was filtered. The filtrate was evaporated in a rotary evaporator and the residue was dissolved in 20 ml. of ethanol. This solution was added to a solution of 1.6 g. of sodium in 150 ml. of ethanol. After stirring at room temperature for 5 minutes, the mixture was diluted with water and was acidified with conc. hydrochloric acid. The precipitate which formed was collected, air dried and was recrystallized from ethyl acetate to afford 2.1 g. of the title product, m.p. 157°-159° C.

Fuente