Réaction #574424

Équation de réaction

(1-ethoxyethylidene)malononitrile

2-methylcyclopentylhydrazine hydrochloride

sodium methoxide

→

1-(2-methylcyclopentyl)-3-methyl-5-amino-1H-pyrazole-4-carbonitrile

Rendement 56.2%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was heated
2. 2
   Températureto reflux
3. 3
   workup.STIRRINGwas stirred for 5 hours
4. 4
   AutreThe solvent was removed in vacuo
5. 5
   Autrethe residue was partitioned between chloroform and water
6. 6
   AutreThe organic layer was separated
7. 7
   Extractionthe aqueous layer was extracted with chloroform three times
8. 8
   LavageThe combined organic layers were washed with brine
9. 9
   Séchagedried over anhydrous MgSO4
10. 10
    Autrethe solvent was removed in vacuo
11. 11
    LavageThe residue was washed with ether

Mode opératoire

To a solution of 2-methylcyclopentylhydrazine hydrochloride (7.4 g, 48.8 mmol) in ethanol (100 ml) was added sodium methoxide (2.6 g, 48.8 mmol). The resulting white suspension was stirred for 10 minutes at room temperature and then (1-ethoxyethylidene)malononitrile (6.7 g, 48.8 mmol) was added. The reaction mixture was heated to reflux and was stirred for 5 hours. The solvent was removed in vacuo and the residue was partitioned between chloroform and water. The organic layer was separated and the aqueous layer was extracted with chloroform three times. The combined organic layers were washed with brine, then dried over anhydrous MgSO4. The solution was passed through a plug of silica gel and the solvent was removed in vacuo. The residue was washed with ether to afford 5.6 g (56%) of 1-(2-methylcyclopentyl)-3-methyl-5-amino-1H-pyrazole-4-carbonitrile as a white powder, m.p. 158°-159° C.

Source