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

HRID 19757

반응식

HRID 19757 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 237308081-(4-Chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid수율 78.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-899dc733b4e749268b1e665b8dbf2e09
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745476B2

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