Benzoylacetone → 1-(4-Methoxyphenyl)-3-methyl-5-phenyl-1H-pyrazole

HRID 903993Notes

Reaction equation

HRID 903993 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.[C:12]1([C:18](=O)[CH2:19][C:20](=O)[CH3:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:19][C:20]([CH3:21])=[N:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7166BenzoylacetoneHCID 11430Potassium CarbonateHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 112655551-(4-Methoxyphenyl)-3-methyl-5-phenyl-1H-pyrazoleYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8.7 parts of (4-methoxyphenyl)hydrazine hydrochloride, 8.1 parts of 1-phenyl-1,3-butanedione, 7 parts of potassium carbonate and 160 parts of ethanol is stirred and refluxed for 20 hours. The reaction mixture is cooled and poured onto water. The product is extracted twice with 2,2'-oxybispropane. The combined extracts are washed with water, dried, filtered and evaporated. The residue is crystallized twice from petroleumether. The product is filtered off and dried, yielding 7 parts (53%) of 1-(4-methoxyphenyl)-3-methyl-5-phenyl-1H-pyrazole; mp. 110° C.

Workup

  1. temperaturerefluxed for 20 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. extractionThe product is extracted twice with 2,2'-oxybispropane
  5. washThe combined extracts are washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized twice from petroleumether
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-44ebcc8e1b154edfa872374ce993817d
Source dataset
uspto-grants-1980_10
Patent number
US04229581

Reaction notes

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