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

HRID 2285962Notes

Reaction equation

HRID 2285962 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 an 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 representing a yield of 72%.

Workup

  1. temperaturewas 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-7dae56299a174baeaeb02f88fcefd9a8
Source dataset
uspto-grants-1982_04
Patent number
US04325962

Reaction notes

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