Cinnamoylbenzene → 3,5-diphenyl-4,5-dihydro-1H-pyrazole

HRID 597578Notes

Reaction equation

HRID 597578 reaction equation
[CH:1](=[CH:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:18][NH2:19]>CO>[C:2]1([C:1]2[CH2:8][CH:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:19][N:18]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7189CinnamoylbenzeneHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 36838443,5-diphenyl-4,5-dihydro-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

There are reacted 12.5 parts of benzalacetophenone and 3.1 parts (by volume) of hydrazine hydrate in methanol to form 3,5-diphenyl-2-pyrazoline. To the latter is added then 5% palladium on carbon catalyst (2 parts) and the reaction mixture is heated at reflux for 1 hour and 20 minutes. The product, 3,5-diphenylpyrazole, is obtained in 97.8% yield.

Sources & evidence

ORD record
ord-2d41dc71d6f54a0daae33fc335338ec6
Source dataset
uspto-grants-1977_03
Patent number
US04014896

Reaction notes

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