Floctafenine

Floctafenine
Systematic (IUPAC) name
2,3-Dihydroxypropyl 2-{[8-(trifluoromethyl)-4-quinolinyl]amino}benzoate
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
23779-99-9
N02BG04
PubChem CID 3360
DrugBank DB08976 
ChemSpider 3243
Chemical data
Formula C20H17F3N2O4
406.355 g/mol

Floctafenine is a non-steroidal anti-inflammatory drug (NSAID).

Synthesis

Flocatfenine synthesis: DE 1815467; eidem, U.S. Patent 3,644,368 Roussel Uclaf; [1]

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.