Hydrochloric Acid → 1-(5-Methoxy-2-pyridyl)-5-phenylpyrazole-3-carboxylic acid

HRID 1437260Notes

Reaction equation

HRID 1437260 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][N:20]=2)[N:9]=1)=[O:7])C.Cl>CO.O1CCCC1>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([N:10]2[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:12][C:8]([C:6]([OH:7])=[O:5])=[N:9]2)=[N:20][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 684408421-(5-Methoxy-2-pyridyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 230905441-(5-Methoxy-2-pyridyl)-5-phenylpyrazole-3-carboxylic acidYield 94.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 1N sodium hydroxide (3.5 mL) was added to the above-obtained 1-(5-methoxy-2-pyridyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (700 mg) in a mixture of methanol (7 mL) and tetrahydrofuran (7 mL), followed by stirring at room temperature for 2 hours. To the reaction mixture, under cooling with ice, aqueous 1N hydrochloric acid (3.6 mL) was added. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, to thereby give the title compound as a solid (602 mg, 94%).

Workup

  1. additionwas added
  2. customThe mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate anhydrate
  5. filtrationfollowed by filtration
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ae4243e50d724524983fa8512c615cf1
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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