130191-66-1Relevant articles and documents
SELECTIVE CLEAVAGE OF THE ETHER AND AMIDE BONDS IN N-(2,4-DIFLUOROPHENYL)-2--3-PYRIDINECARBOXAMIDE (DIFLUFENICAN)
Rouchaud, Jean,Gustin, Fabrice,Moulart, Claude,Herin, Marc
, p. 339 - 344 (2007/10/02)
Heated to reflux in water containing 8 gpercent KOH, the herbicide diflufenican -3-pyridinecarboxamide, 1> was selectively transformed into 2--3-pyridinecarboxylic acid (2) plus 2,4-difluoroaniline (5); after 60 hr of heating, 27percent of the initial diflufenican was transformed, yielding 21percent (molepercent relative to initial diflufenican) of compound 2.Heated to reflux in a mixture of acetic acid + concentrate hydrochloric acid, diflufenican was transformed into a mixture of N-(2,4-difluorophenyl)-2-hydroxy-3-pyridinecarboxamide (3) and 2-hydroxy-3-carboxypyridine (4) plus 2,4-difluoroaniline (5) and 3-trifluoromethylphenol (6); after 48 hr of heating, diflufenican was completely transformed, yielding 28percent (molepercent relative to initial diflufenican) of compound 3, and 57percent of compound 4.The base catalyzed hydrolysis thus selectively yielded compound 2; the acid catalyzed one yielded compounds 3 + 4: diflufenican first was transformed into compound 3, which thereafter was transformed into compound 4.