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

HRID 850074Notes

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][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])#[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][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution (15 ml) of ethyl 1-(3-cyano-4-(3-methylbutoxy)phenyl)pyrazole-4-carboxylate (1.6 g) in ethanol was added 1.5 N aqueous sodium hydroxide solution (4 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 ethyl acetate to give 0.97 g of 1-(3-cyano-4-(3-methylbutoxy)phenyl)pyrazole-4-carboxylic acid, melting point 210-211° C.

Workup

customAfter the completion of the reaction
customThe precipitated crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-0dd89eaeb7cd471c9e023e0df7f10aaf
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015829

Reaction notes

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