Phenylhydrazine → 3-Amino-1-phenylpyrazole

HRID 1388718Notes

Reaction equation

HRID 1388718 reaction equation
[Na].[C:2]1([NH:8][NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10](#[N:13])[CH:11]=[CH2:12]>C(O)C>[NH2:13][C:10]1[CH2:11][CH2:12][N:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 7855AcrylonitrileHCID 5360545Sodium

Product 1

HCID 987363-Amino-1-phenylpyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2.0 g. amount of sodium metal is dissolved in 100 ml. of absolute ethanol, then 40.0 ml. of phenylhydrazine is added followed by 26.0 ml. of acrylonitrile. The reaction mixture is refluxed for 3 hours with exothermic crystallization of a product. The product is collected by filtration and washed with 95% ethanol. The material is recrystallized from dichloromethane-benzene to give 43.6 g. of the desired product as a solid, m.p. 168°-170.5° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hours with exothermic crystallization of a product
  2. filtrationThe product is collected by filtration
  3. washwashed with 95% ethanol
  4. customThe material is recrystallized from dichloromethane-benzene
  5. customto give 43.6 g

Sources & evidence

ORD record
ord-a482455446934393837fb101a9aefa57
Source dataset
uspto-grants-1984_02
Patent number
US04432991

Reaction notes

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