Water → 1-(4-Chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid

HRID 19757

Reaktionsgleichung

Reaktionsgleichung von HRID 19757
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][C:10]([C:19]([O:21]CC)=[O:20])=[N:9]2)=[CH:4][CH:3]=1.O.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][C:10]([C:19]([OH:21])=[O:20])=[N:9]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23730695Ethyl 1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylate

Produkt 1

HCID 237308081-(4-Chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acidAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Part C: To a stirred suspension of ethyl 1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxylate (23.0 gram, 0.07 mol) in methanol (200 ml) is added water (15 ml) and concentrated NaOH (10 ml) and the resulting solution is heated at reflux temperature for 2 hours. The methanol is partly removed by evaporation and the residue is dissolved in a mixture of water and ethyl acetate. Ice, concentrated HCl (20 ml) and ethyl acetate are successively added, the ethyl acetate layer collected, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue is washed with diethyl ether (100 ml) and diisopropyl ether respectively, to give 1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxylic acid (16.46 gram, 78% yield). Melting point: 177-179° C.

Aufarbeitung

  1. temperaturethe resulting solution is heated
  2. temperatureat reflux temperature for 2 hours
  3. customThe methanol is partly removed by evaporation
  4. dissolutionthe residue is dissolved in a mixture of water and ethyl acetate
  5. additionIce, concentrated HCl (20 ml) and ethyl acetate are successively added
  6. customthe ethyl acetate layer collected
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. washThe resulting residue is washed with diethyl ether (100 ml) and diisopropyl ether respectively

Quellen und Nachweise

ORD-Eintrag
ord-899dc733b4e749268b1e665b8dbf2e09
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745476B2

Verknüpfte Notizen

Wird geladen…