Water → Ethyl 1-(3-cyano-4-hydroxyphenyl)pyrazole-4-carboxylate

HRID 850065Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution (280 ml) of ethyl 1-(3-cyano-4-methoxyphenyl)pyrazole-4-carboxylate (28 g) in dichloroethane was added aluminum chloride (47.6 g with stirring, and the mixture was heated at 70° C. for 4 hours. After the completion of the reaction, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was recrystallized from ethyl acetate to give 22.5 g of ethyl 1-(3-cyano-4-hydroxyphenyl)pyrazole-4-carboxylate, melting point 233-234° C. ##STR19##

Workup

customAfter the completion of the reaction
extractionextracted with ethyl acetate
washwashed with water
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-a4eebd45252244e5891ad6b4c86300ff
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015829

Reaction notes

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