Sodium Hydroxide → 1-Methyl-1H-pyrazole-4-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:11])[CH:10]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:11][N:9]1[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (300 mg, 1.95 mmol) in ethanol cooled to 0° C. was treated with a 1N aqueous sodium hydroxide solution. The reaction was then warmed to 25° C. and was stirred at 25° C. for 18 h. At this time, the reaction was concentrated in vacuo and acidified to pH=2 with a 1N aqueous hydrochloric acid solution. This solution was extracted with ethyl acetate (3×50 mL). The organics were washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and dried in vacuo to afford 1-methyl-1H-pyrazole-4-carboxylic acid (193 mg, 78.5%) as a white solid: LR-MS for C5H6N2O2 (M−H)+ at m/z=125.
Workup
- concentrationAt this time, the reaction was concentrated in vacuo
- extractionThis solution was extracted with ethyl acetate (3×50 mL)
- washThe organics were washed with a saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customdried in vacuo
Sources & evidence
- ORD record
- ord-55e0360488dd47738c9076875af4ba08
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07135475B2
Reaction notes
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