Hydrochloric Acid → 1-methyl-3-phenyl-1H-pyrazole-5-carboxylic acid

HRID 2298022Notes

Reaction equation

HRID 2298022 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:17])[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=1)=[O:5])C.CO.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH3:17][N:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 4166529Ethyl 1-methyl-3-phenyl-1H-pyrazole-5-carboxylate

Product 1

HCID 75376251-methyl-3-phenyl-1H-pyrazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-5-phenyl-2H-pyrazole-3-carboxylic acid ethyl ester (0.32 g, 1.39 mmol) was dissolved in 4.5 mL of tetrahydrofuran, 1.5 mL of methanol and 1.5 mL of water, and treated with lithium hydroxide hydrate (0.12 g, 2.78 mmol). After stirring at room temperature overnight, the mixture was acidified (pH =1) with hydrochloric acid, and extracted with ethyl acetate (3×10 mL) and the combined organic phases washed with 10 mL of brine. The organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford a quantitative yield of the title compound.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washthe combined organic phases washed with 10 mL of brine
  3. dry with materialThe organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f08bbc147ae45febd6c3ced15999285
Source dataset
uspto-grants-2002_12
Patent number
US06492401B1

Reaction notes

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