Reacción #94900

Ecuación de reacción

N-decyl-3-phenyl-3-(4-nitrophenyl)propenamide

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title compound

N-Decyl-3-phenyl-3-(4-aminophenyl)propenamide

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONthe temperature was between 85° and 90° C. during the addition
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Filtraciónthe reaction mixture was filtered
4. 4
   Lavadothe solids were washed with further hot acetic acid
5. 5
   OtroThe combined acetic acid solutions were evaporated in vacuo
6. 6
   Otrothe residue was partitioned between ethyl acetate and water
7. 7
   OtroThe ethyl acetate layer was removed
8. 8
   Lavadowashed with water
9. 9
   Otrodried
10. 10
    OtroEvaporation in vacuo
11. 11
    Otrogave an oil which
12. 12
    OtroThe solid was recrystallized from isopropyl ether
13. 13
    Otrogiving 2.3 g

Procedimiento

To a stirred solution of 5.6 g. of N-decyl-3-phenyl-3-(4-nitrophenyl)propenamide in 80 ml. of glacial acetic acid, at 85° C., was added, portionwise, during 20 minutes, 3.85 g. of iron powder. The reaction was exothermic and the temperature was between 85° and 90° C. during the addition. After the addition, the reaction mixture was filtered and the solids were washed with further hot acetic acid. The combined acetic acid solutions were evaporated in vacuo and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was removed, washed with water, and dried. Evaporation in vacuo gave an oil which solidified. The solid was recrystallized from isopropyl ether, giving 2.3 g. of the title compound, m.p. 90°-100° C.

Fuente