Sulfuric Acid → 1-[(4-Methoxy)phenyl]-5-(methoxycarbonyl)pyrazole-3-carboxylic acid

HRID 610140노트

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HRID 610140 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]([C:18]([O:20]C)=[O:19])=[N:10]2)=[CH:5][CH:4]=1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]([C:18]([OH:20])=[O:19])=[N:10]2)=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 11748281Dimethyl 1-[(4-methoxy)phenyl]pyrazole-3,5-dicarboxylate

생성물 1

HCID 542100671-[(4-Methoxy)phenyl]-5-(methoxycarbonyl)pyrazole-3-carboxylic acid수율 63.2%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a solution of dimethyl 1-[(4-methoxy)phenyl]pyrazole-3, 5-dicarboxylate (32.7 g, 110 mmol) in 50 mL of dioxane and 100 mL of water was added concentrated sulfuric acid (1.50 mL, 28.2 mmol). The resulting solution was stirred at 100° C. for 18 h and then cooled to room temperature. The reaction was made basic with potassium carbonate and then extracted with ether to remove unreacted diester. The aqueous layer was acidified with HCl and was extracted twice with ethyl acetate. The combined organics were washed with brine, dried (MgSO4) and concentrated to afford 19.2 g (63%) of the title compound along with 5.0 g (15%) of unreacted starting material. The title compound was used without further purification. LRMS (ES-): 274.9 (M-H)-.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with ether
  3. customto remove unreacted diester
  4. extractionwas extracted twice with ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-99c74636750f43bca107a8b45e3d8abf
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998424

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