Reacción #574446

Ecuación de reacción

cyclopentyl hydrazine hydrochloride

sodium methoxide

(1-methoxyphenylethylidene)malononitrile

→

1-cyclopentyl-3-phenylmethyl-5-amino-1H-pyrazole-4-carbonitrile

Rendimiento 26.0%

Disolventes

ethanol

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturato reflux
3. 3
   TemperaturaThe reaction mixture was refluxed for 6.5 hours
4. 4
   Otrothe solvent was removed in vacuo
5. 5
   OtroThe residue was partitioned between chloroform and water
6. 6
   Otrothe organic layer was separated
7. 7
   Extracciónthe aqueous layer was extracted with chloroform (3×75 ml)
8. 8
   LavadoThe combined organic layers were washed with brine
9. 9
   Secadodried over anhydrous MgSO4
10. 10
    Concentraciónconcentrated in vacuo

Procedimiento

A mixture of cyclopentyl hydrazine hydrochloride (1.4 g, 10.2 mmol), sodium methoxide (0.55 g, 10.2 mmol) and ethanol (30 ml) was heated to reflux and then (1-methoxyphenylethylidene)malononitrile (2.0 g, 10.2 mmol) in ethanol (15 ml) was added dropwise over 1 hour. The reaction mixture was refluxed for 6.5 hours and the solvent was removed in vacuo. The residue was partitioned between chloroform and water, the organic layer was separated and the aqueous layer was extracted with chloroform (3×75 ml). The combined organic layers were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo to afford 0.7 g (26%) of 1-cyclopentyl-3-phenylmethyl-5-amino-1H-pyrazole-4-carbonitrile as white flakes, m.p. 180°-182° C. when recrystallized from ethyl acetate and dried for 18 hours at 90° C. in high vacuum.

Fuente