Hydrochloric Acid → 1-methyl-4-(5-methylpyridin-2-yl)-1H-pyrazole-5-carboxylic acid

HRID 60118Notes

Reaction equation

[OH-].[Na+].[CH3:3][N:4]1[C:8]([C:9]([O:11]C)=[O:10])=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:6]=[N:5]1.Cl>CO>[CH3:3][N:4]1[C:8]([C:9]([OH:11])=[O:10])=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:6]=[N:5]1

Participants

Conditions

Temperature: 70 °C

Procedure

An aqueous solution (1.3 ml) of sodium hydroxide (50 mg) was added to a methanol (1.3 ml) solution of the methyl 1-methyl-4-(5-methylpyridin-2-yl)-1H-pyrazole-5-carboxylate (100 mg) obtained in (Example 1.1) <Step 2>. The obtained mixture was stirred at 70° C. for 1 hour. Thereafter, 1 N hydrochloric acid was added to the reaction solution to adjust the pH value to pH 5, and the reaction mixture was then extracted with methylene chloride three times. The organic layer was successively washed with water and a saturated saline, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and a mixed solution of diethyl ether and heptane (1:1) was added to the obtained residue to solidify it, so as to obtain the title compound (74 mg) in the form of a white solid.

Workup

customobtained in (Example 1.1) <Step 2>
extractionthe reaction mixture was then extracted with methylene chloride three times
washThe organic layer was successively washed with water
dry with materiala saturated saline, and was then dried over anhydrous sodium sulfate
distillationThe solvent was distilled away under reduced pressure
additiona mixed solution of diethyl ether and heptane (1:1) was added to the obtained residue

Sources & evidence

ORD record: ord-140a1cd591e64f09a92a051819860a9a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440970B2

Reaction notes

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