Phenylhydrazine → 3-Amino-1-phenyl-5-p-tolyl-2-pyrazoline

HRID 1388724Notes

Reaction equation

HRID 1388724 reaction equation
[Na].[C:2]1([NH:8][NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH:20]=[CH:19][C:14]([CH:15]=[CH:16][C:17]#[N:18])=[CH:13][CH:12]=1>C(O)C>[NH2:18][C:17]1[CH2:16][CH:15]([C:14]2[CH:13]=[CH:12][C:11]([CH3:10])=[CH:20][CH:19]=2)[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 342423-(4-Methylphenyl)prop-2-enenitrileHCID 5360545Sodium

Product 1

HCID 130641903-Amino-1-phenyl-5-p-tolyl-2-pyrazoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1.0 g. amount of sodium metal is dissolved in 100 ml. of absolute ethanol, then 20.0 ml. of phenylhydrazine is added followed in 5 minutes by 24.0 ml. of (mixed cis and trans) 4-methyl cinnamonitrile. The reaction mixture is refluxed for 4 hours then is cooled. The precipitate is collected by filtration then is recrystallized from acetone-hexane after treatment with activated charcoal to give 14.25 g. of the desired product as pale orange needles, m.p. 165°-166.5° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. temperaturethen is cooled
  3. filtrationThe precipitate is collected by filtration
  4. customthen is recrystallized from acetone-hexane after treatment with activated charcoal
  5. customto give 14.25 g

Sources & evidence

ORD record
ord-f7b5aa2ec4c942b0a7dde3872f29782c
Source dataset
uspto-grants-1984_02
Patent number
US04432991

Reaction notes

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