Reaction #155900

Reaction equation

1-phenylhydrazine

2-(1-ethoxyethylidene)malononitrile

ethoxymethylene malononitrile

→

5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile

Solvents

ethanol

Conditions

Workup

1. 1
   OtherInto a 250-mL 3-necked round-bottom flask, was placed
2. 2
   Otherat room temperature
3. 3
   Otherat room temperature
4. 4
   workup.ADDITIONAfter about half of the addition
5. 5
   Temperaturethe solution was carefully heated to boiling
6. 6
   Temperaturethe resulting solution was heated
7. 7
   Temperatureto reflux for 4 hr
8. 8
   TemperatureThe resulting mixture was then cooled with a water/ice bath
9. 9
   Filtrationthe solids were collected by filtration

Procedure

Into a 250-mL 3-necked round-bottom flask, was placed a solution of 1-phenylhydrazine (31.5 g, 291.67 mmol, 1.14 equiv) in ethanol (105 mL) at room temperature. To the resulting mixture was then added 2-(1-ethoxyethylidene)malononitrile (35 g, 257.35 mmol, 1.00 equiv) in several batches at room temperature. After about half of the addition was completed, the solution was carefully heated to boiling. After all the ethoxymethylene malononitrile was added, the resulting solution was heated to reflux for 4 hr. The resulting mixture was then cooled with a water/ice bath, and the solids were collected by filtration to yield 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile as a yellow solid.

Source