Acetic Acid → 3-Methyl-1-phenyl-5-(p-chlorophenyl)pyrazol-4-acetic acid

HRID 615010Notes

Reaction equation

HRID 615010 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][CH:6]([C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:7]([CH3:9])=O)C.[C:20]1([NH:26][NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)(=O)C>C(O)C>[CH3:9][C:7]1[C:6]([CH2:5][C:4]([OH:3])=[O:19])=[C:10]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[N:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:27]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7516PhenylhydrazineHCID 544551833-(p-Chlorobenzoyl)-levulinic acid ethyl ester

Product 1

HCID 205427343-Methyl-1-phenyl-5-(p-chlorophenyl)pyrazol-4-acetic acidYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.5 grams 3-(p-chlorobenzoyl)-levulinic acid ethyl ester, 4.9 grams phenyl-hydrazine, 2.8 grams glacial acetic acid and 10 milliliters ethanol were mixed and the mixture was heated to the boiling temperature under reflux for 3.5 hours. The reaction mixture was evaporated and 100 milliliters benzene were added to the residue. The pH of the solution was adjusted to 3, followed by extraction with water. The benzene phase was evaporated and 30 milliliters ethanol and 20 milliliters 2N aqueous sodium hydroxide added to the residue. The mixture was heated to the boiling temperature under reflux for 1 hour, and thereafter worked up and the free acid recovered in accordance with a procedure analogous to that set out in Example (1b). 9.6 grams 3-methyl-1-phenyl-5-(p-chlorophenyl)pyrazol-4-acetic acid, melting at 174°-177° C., were obtained represeing a yield of 72%.

Workup

  1. temperaturethe mixture was heated to the boiling temperature
  2. temperatureunder reflux for 3.5 hours
  3. customThe reaction mixture was evaporated
  4. addition100 milliliters benzene were added to the residue
  5. extractionfollowed by extraction with water
  6. customThe benzene phase was evaporated
  7. addition30 milliliters ethanol and 20 milliliters 2N aqueous sodium hydroxide added to the residue
  8. temperatureThe mixture was heated to the boiling temperature
  9. temperatureunder reflux for 1 hour
  10. customthe free acid recovered in accordance with a procedure analogous to

Sources & evidence

ORD record
ord-203aaef48e3f48b5874acdf96252cbe8
Source dataset
uspto-grants-1979_03
Patent number
US04146721

Reaction notes

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