3-Phenylprop-2-enenitrile → 1-(3-Chlorophenyl)-5-phenyl-4,5-dihydro-1h-pyrazol-3-amine

HRID 544632Notes

Reaction equation

HRID 544632 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[C:11](#[N:20])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[NH2:20][C:11]1[CH2:12][CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=2)[N:10]=1

Participants

5

Reactant 3

HCID 746673-Phenylprop-2-enenitrileHCID 75332(3-Chlorophenyl)hydrazineHCID 5360545Sodium

Product 1

HCID 133095141-(3-Chlorophenyl)-5-phenyl-4,5-dihydro-1h-pyrazol-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 0.6 g. amount of sodium metal is dissolved in 100 ml. of absolute ethanol, then 14.76 g. of m-chlorophenylhydrazine is added followed in 5 minutes by 12.92 g. of cinnamonitrile. The reaction mixture is refluxed for 6 hours, then cooled in an ice-bath. The precipitate formed is collected by filtration, then is dissolved in dichloromethane. This solution is passed through a short column of a hydrous magnesium silicate. The effluent is heated to reflux on a steam bath and hexane is added until a precipitate occurs. The product is collected, then is recrystallized from dichloromethane-hexane to give 7.55 g. of the product of the Example as salmon colored needles, m.p. 164°-165° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 6 hours
  2. temperaturecooled in an ice-bath
  3. customThe precipitate formed
  4. filtrationis collected by filtration
  5. dissolutionis dissolved in dichloromethane
  6. temperatureThe effluent is heated
  7. temperatureto reflux on a steam bath
  8. additionhexane is added until a precipitate
  9. customThe product is collected
  10. customis recrystallized from dichloromethane-hexane
  11. customto give 7.55 g

Sources & evidence

ORD record
ord-26a48b3f007b48fbb6cc0336caf40ab4
Source dataset
uspto-grants-1984_05
Patent number
US04451479

Reaction notes

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