Chemistry:Floctafenine
From HandWiki
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.[1][2][3] 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. The displacement of chlorine with methyl anthranilate (4) then affords the coupled intermediate (5). An ester interchange of that product with glycerol leads to the glyceryl ester, floctafenine (6).
References
- ↑ Allais, André & Jean Meier, "Neue Chinolidinderivate und Verfahren zu ihrer Herstellung [Novel quinolidine derivatives and processes for their preparation]", DE patent 1815467A1, published 1969-07-24
- ↑ U.S. Patent 3,644,368 Roussel Uclaf
- ↑ "A New, Convenient Synthesis of Glafenine and Floctafenine". Synthesis 1980: 54–55. 1980. doi:10.1055/s-1980-28923.
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