ChemicalBook CAS DataBase List Flufenamic acid

Flufenamic acid synthesis

7synthesis methods

Product Name:Flufenamic acid
CAS Number:530-78-9
Molecular formula:C14H10F3NO2
Molecular Weight:281.23

Flufenamic acid, N-(α,α,α-trifluoro-m-tolyl)anthranylic acid (3.2.18), is synthesized by the reaction of 2-chlorobenzoic acid with 3-trifluoromethylaniline in the presence of potassium carbonate and copper filings [78,79].

Benzoic acid,2-[[3-(trifluoromethyl)phenyl]amino]-, methyl ester

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Yield:530-78-9 55%

Reaction Conditions:

with water;potassium hydroxide in ethanol at 100;Inert atmosphere;

Steps:

General Procedure B
To a solution of the methyl ester (1 equiv) in EtOH (0.2 M) was added KOH (2 equiv per ester) in water (0.2 M) at room temperature. The reaction mixture was allowed to stir at 100 °C for 1-6 h. Once the reaction appeared complete by TLC analysis, EtOH was evaporated from the reaction mixture, the resultant solution was cooled to 0 °C and acidified to pH 2 w 2M aq HCl. The resultant precipitated product was collected by vacuum filtration and washed with water.

References:

Adeniji, Adegoke O.;Twenter, Barry M.;Byrns, Michael C.;Jin, Yi;Winkler, Jeffrey D.;Penning, Trevor M. [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 5,p. 1464 - 1468] Location in patent:supporting information; experimental part

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