Phenylhydrazine → 3-Amino-1-phenylpyrazole

HRID 2198970Notes

Reaction equation

HRID 2198970 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-84f08e60732a44dd904b5c6e8294a022
Source dataset
uspto-grants-1982_11
Patent number
US04360680

Reaction notes

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