Hydrochloric Acid → 3,5-diethoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoic acid

HRID 1096981Notes

Reaction equation

C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[C:7]([C:13]2[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=2)=[C:6]([O:19][CH2:20][CH3:21])[CH:5]=1.Cl>CO.C1COCC1.[OH-].[Na+]>[CH2:20]([O:19][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH2:11][CH3:12])[C:7]=1[C:13]1[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=1)[C:3]([OH:22])=[O:2])[CH3:21]

Participants

Conditions

Temperature: 50 °C

Procedure

3,5-Diethoxy-4-(1-methyl-1H-pyrazol-4-yl)-benzoic acid methyl ester (895 mg) was dissolved in a mixed methanol/THF solution (16 mL, 5/3), aqueous 1 M NaOH solution (6 mL) was added to it, and stirred at 50° C. for 5 hours. The reaction liquid was cooled to room temperature, and aqueous 1 M HCl solution (6 mL) was added to it, and the solvent was evaporated away under reduced pressure. The resulting solid was taken out through filtration, washed with water and ether, and dried under reduced pressure to obtain the title compound as a pale yellow solid.

Workup

additionwas added to it
customThe reaction liquid
temperaturewas cooled to room temperature
customthe solvent was evaporated away under reduced pressure
filtrationThe resulting solid was taken out through filtration
washwashed with water and ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-4e9310e6064741a89cc3da007de56a35
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138197B2

Reaction notes

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