Acetic Acid → 1-[3-Cyano-4-(1-ethylpropoxy)phenyl]-1H-pyrazole-4-carboxylic acid

HRID 850073Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution (10 ml) of ethyl 1-(3-cyano-4-(1-ethylpropoxy)phenyl)pyrazole-4-carboxylate (0.8 g) in ethanol was added 2 N aqueous sodium hydroxide solution (1.5 ml) with stirring, and the mixture was heated at 80° C. for 30 minutes. After the completion of the reaction, the reaction mixture was poured into water and neutralized with acetic acid. The precipitated crystals were recrystallized from a mixed solvent of ethyl alcohol and water to give 0.6 g of 1-(3-cyano-4-(1-ethylpropoxy)phenyl)pyrazole-4-carboxylic acid, melting point 142-144° C.

Workup

customAfter the completion of the reaction
customThe precipitated crystals were recrystallized from a mixed solvent of ethyl alcohol and water

Sources & evidence

ORD record: ord-e87a04a64dd14f83848934590f1ad7e6
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015829

Reaction notes

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