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

HRID 19757

反応式

HRID 19757 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-899dc733b4e749268b1e665b8dbf2e09
出典データセット
uspto-grants-2010_06
特許番号
US07745476B2

関連ノート

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