Floctafenine

Floctafenine
Clinical data
AHFS/Drugs.com International Drug Names
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
ECHA InfoCard 100.041.696
Chemical and physical data
Formula C20H17F3N2O4
Molar mass 406.355 g/mol
3D model (JSmol)

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

Synthesis

The scheme involves first the conversion of ortho-trifluoromethyl aniline (1) to a quinolol. The compound is thus condensed with EMME (Ethoxy Methylene Malonic Diethyl Ester) 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. There is thus obtained the NSAID floctafenine.

See also

References

  1. Mouzin, G.; Cousse, H.; Autin, J. M. (1980). "A New, Convenient Synthesis of Glafenine and Floctafenine". Synthesis. 1980: 54. doi:10.1055/s-1980-28923.


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