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

HRID 68718

Reaction equation

HRID 68718 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[C:12](=[C:14]([C:17]#[N:18])[C:15]#[N:16])[CH3:13])C.C(OC=C(C#N)C#N)C>C(O)C>[NH2:18][C:17]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=[C:12]([CH3:13])[C:14]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 671522-(Ethoxymethylene)propanedinitrileHCID 79450(1-Ethoxyethylidene)malononitrile

Product 1

HCID 2198585-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. customInto a 250-mL 3-necked round-bottom flask, was placed
  2. customat room temperature
  3. customat room temperature
  4. additionAfter about half of the addition
  5. temperaturethe solution was carefully heated to boiling
  6. temperaturethe resulting solution was heated
  7. temperatureto reflux for 4 hr
  8. temperatureThe resulting mixture was then cooled with a water/ice bath
  9. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-f135ab60af0c414f928bdb7fa3b2c11f
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Linked notes

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