Hydrochloric Acid → HCID 619059, compound

HRID 615009Notes

Reaction equation

HRID 615009 reaction equation
C([O:3][C:4](=[O:18])[CH2:5][CH:6]([C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([CH3:9])=O)C.[C:19]1([NH:25][NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C(O)CCC>[CH3:9][C:7]1[C:6]([CH2:5][C:4]([OH:3])=[O:18])=[C:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 53811318HCID 53811318, compound

Product 1

HCID 619059HCID 619059, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

3.0 grams 3-benzoyl-levulinic acid-ethyl ester, 1.3 gram phenyl-hydrazine, 0.15 milliliter 2N aqueous hydrochloric acid and 25 milliliters n-butanol were mixed and the mixture heated to boiling temperature under reflux for 1.5 hour. The reaction mixture was evaporated in vacuo and benzene added to the residue. The benzene solution was adjusted to a pH of 4 and extracted with water. The benzene was evaporated from the solution, and 15 milliliters ethanol and 20 milliliters 1N aqueous sodium hydroxide were added to the residue and the mixture heated to the boiling temperature. The mixture was then worked up and the free acid recovered in accordance with the procedure set out in Example (1b). 3.3 grams 3-methyl-1,5-diphenyl-pyrazol-4-acetic acid, melting at 159°-161° C., were obtained representing a yield of 93%.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1.5 hour
  3. customThe reaction mixture was evaporated in vacuo and benzene
  4. additionadded to the residue
  5. extractionextracted with water
  6. customThe benzene was evaporated from the solution, and 15 milliliters ethanol and 20 milliliters 1N aqueous sodium hydroxide
  7. additionwere added to the residue
  8. temperaturethe mixture heated to the boiling temperature
  9. customthe free acid recovered in accordance with the procedure

Sources & evidence

ORD record
ord-708a2112fcc847329b469a496b686093
Source dataset
uspto-grants-1979_03
Patent number
US04146721

Reaction notes

Loading…