Nitric esters from derivatives of 2-(2,6-dihalophenylamino) phenylacetoxyacetic acid and their preparation process

Process of preparing nitric esters from derivatives of 2-(2,6-dihalophenylamino) phenylacetoxyacetic acid with the general formula (I):

• ##STR17## where:
• A is fluorine, chlorine or bromine;
• X is O, NH or NR where R is a linear or branched alkyl chain of 1 to 6 carbon atoms;
• R.sub.1 and R.sub.2 mean, independently, hydrogen or a linear or branched alkyl chain of 1 to 6 carbon atoms;
• n is a number between 1 to 10,
• characterized by condensing the 2-(2,6-dihalophenylamino) phenylacetoxyacetic acid with the formula (IV) where A is fluorine, chlorine or bromine ##STR18## with a derivative with the general formula (V) ##STR19## where Y can be OH, NH.sub.2 or NHR, where R is a linear or branched alkyl chain of 1 to 6 carbon atoms, R.sub.1 and R.sub.2 mean, independently, hydrogen or a linear or branched alkyl chain of 1 to 6 carbon atoms and n is a number between 1 to 10, in presence of an suitable condenser agent in an aprotic organic solvent.

Process of preparing nitric esters from derivatives of 2-(2,6-dihalophenylamino) phenylacetoxyacetic acid having the general formula (I):

• ##STR20## wherin:
• A is fluorine, chlorine or bromine;
• X means O, NH or NR where R means a linear or ramified alkyl chain of 1 to 6 carbon atoms;
• R.sub.1 and R.sub.2 is, independently, hydrogen or a linear or branched alkyl chain of 1 to 6 carbon atoms;
• n is a number between 1 to 10,
• characterized by having the following stages:
• (i) condensation of 2-(2,6-dihalophenylamino) phenylacetoxyacetic acid with the formula IV:
• ##STR21## where:
• A is fluorine, chlorine or bromine with a general formula compound with the formula VI:
• ##STR22## where Y is OH, NH.sub.2 or NHR where R, R.sub.1, R.sub.2 and n have the meaning above mentioned and Z is chlorine or bromine, in presence of suitable condensation agent to provide the compound with the formula VII:
• ##STR23## where A, R.sub.1, R.sub.2 and Z have the meaning above mentioned and X is O, NH or NR being R a linear or branched alkyl chain of 1 to 6 carbon atoms;
• (ii) optional substitution of the Z halogen of the compound with the formula VII by a iodine atom through the reaction with sodium iodide to provide the compound with the formula VIII:
• ##STR24## iii) displacement of the Z halogen of the compound with the formula VII or, otherwise, of the iodine atom I of the compound with the formula VIII with AgNO.sub.3 in acetonitrile as solvent, to provide the corresponding nitroesters with the formula I.