Hydrochloric Acid → 4,5-Dihydro-3-(4-methoxyphenyl)-5-(4-nitrophenyl)-1-phenyl-1H-pyrazole

HRID 364919Notes

Reaction equation

HRID 364919 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7](=O)[CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[C:22]1([NH:28][NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.[OH-].[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]2[CH2:8][CH:9]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)[N:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:29]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 14798Sodium HydroxideHCID 237433HCID 237433, compound

Product 1

HCID 44365034,5-Dihydro-3-(4-methoxyphenyl)-5-(4-nitrophenyl)-1-phenyl-1H-pyrazoleYield 78.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

14.2 g of 4'-methoxy-4-nitrochalcone was reacted with 5.4 g of phenylhydrazine in 100 ml of ethanol in the presence of 5 ml of hydrochloric acid by refluxing while heating for 6 hours. After neutralizing the reaction mixture with 50 ml of 1N NaOH, 400 ml of water was added thereto. Decantation-water washing was repeated three times. Crystals formed were recrystallized from 200 ml of acetone to obtain 14.7 g of the desired compound. m.p. 168°-173° C.

Workup

  1. temperatureby refluxing
  2. temperaturewhile heating for 6 hours
  3. additionwas added
  4. customCrystals formed
  5. customwere recrystallized from 200 ml of acetone

Sources & evidence

ORD record
ord-90c8b9d09d7044559158e50f312ba1f8
Source dataset
uspto-grants-1986_08
Patent number
US04607006

Reaction notes

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