Floctafenine is a nonsteroidal anti-inflammatory drug (NSAID).

Synthesis

Floctafenine can be synthesized beginning with the conversion of ''ortho''-trifluoromethyl aniline (1) to a quinolol. The compound is then condensed with ethoxy methylene malonic diethyl ester (EMME) and cyclized thermally (2). That intermediate is then saponified; the resulting acid is decarboxylated and finally converted to the 4-chloroquinoline (3) by reaction with

phosphorus oxychloride Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula . It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from pho ...

. The displacement of chlorine with

methyl anthranilate Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid. Its chemical formula is C8H9NO2. It has a strong and fruity grape smell, and one of its key uses is as a flavoring agent. Chem ...

(4) then affords the coupled intermediate (5). An ester interchange of that product with

glycerol Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known ...

leads to the glyceryl ester, floctafenine (6). Flocatfenine synthesis

References

Nonsteroidal anti-inflammatory drugs Quinolines Vicinal diols Trifluoromethyl compounds Anthranilates {{analgesic-stub

Synthesis

See also

References