Acetic Acid → 1-(3-Cyano-4-hexyloxyphenyl)pyrazole-4-carboxylic acid

HRID 850069Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([N:16]2[CH:20]=[C:19]([C:21]([O:23]CC)=[O:22])[CH:18]=[N:17]2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])#[N:2].[OH-].[Na+].O.C(O)(=O)C>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([N:16]2[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[N:17]2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution (20 ml) of ethyl 1-(3-cyano-4-hexyloxyphenyl)pyrazole-4-carboxylate (1.8 g) in ethanol was added 1 N aqueous sodium hydroxide solution (6 ml) with stirring, and the mixture was heated at 50° C. for 1 hour. After the completion of the reaction, the reaction mixture was poured into water and the mixture was neutralized with acetic acid. The precipitated crystals were recrystallized from a mixed solution of dioxane and water to give 1.2 g of 1-(3-cyano-4-hexyloxyphenyl)pyrazole-4-carboxylic acid, melting point 164-165° C.

Workup

customAfter the completion of the reaction
customThe precipitated crystals were recrystallized from a mixed solution of dioxane and water

Sources & evidence

ORD record: ord-736cd474891d4a8286da4a2ac0a6e2a0
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015829

Reaction notes

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