Floctafenine

Floctafenine

Systematic (IUPAC) name
2,3-Dihydroxypropyl 2-{[8-(trifluoromethyl)-4-quinolinyl]amino}benzoate
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	23779-99-9
ATC code	N02BG04 (WHO)
PubChem	CID 3360
DrugBank	DB08976
ChemSpider	3243
Chemical data
Formula	C20H17F3N2O4
Molar mass	406.355 g/mol
SMILES FC(F)(F)c1cccc2c(ccnc12)Nc3ccccc3C(=O)OCC(O)CO
InChI InChI=1S/C20H17F3N2O4/c21-20(22,23)15-6-3-5-13-17(8-9-24-18(13)15)25-16-7-2-1-4-14(16)19(28)29-11-12(27)10-26/h1-9,12,26-27H,10-11H2,(H,24,25) Key:APQPGQGAWABJLN-UHFFFAOYSA-N

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

• Glafenine, a chemically related NSAID

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.