Process for the preparation of deactivated anilines

Abstract

The present invention is directed to a process for the preparation of deactivated anilines, which comprises the step of reacting a compound of formula (I) ##STR1## with a dialkylamide in the presence of a base at elevated temperature, in which: R.sub.1 is chosen from groups whose anions (R.sub.1.sup.-) constitute leaving groups; R.sub.2 and R.sub.4, which may be the same or different, are chosen from hydrogen, hydrocarbon chains, halogens and groups which are electron-attracting (EAG); R.sub.3 is chosen from hydrocarbon chains, halogens and groups which are electron-attracting, preferably through an inductive effect rather than a mesomeric effect; with the proviso that at least one of the groups R.sub.2, R.sub.3, and R.sub.4 is electron-attracting through an inductive effect. A second embodiment of the present invention is directed to a process for the dealkylation of deactivated anilines which comprises the steps of free radical halogenation of the benzyl carbon followed by hydrogenation. A third embodiment of the present invention is directed to a process for the dealkylation of deactivated anilines which comprises the step of reacting an alkylated aniline with an amine in the presence of a catalytic amount of a pyridine salt. A fourth embodiment of the present invention is direct to intermediates for the preparation of deactivated anilines which have the formula (III) Ar--N(--CH.sub.2-x Z.sub.x --R.sub.1 ')(--CH.sub.2-y Z.sub.y --R.sub.2 ') (III) wherein Z represents a halogen atom; R.sub.1 ' and R.sub.2 ', which may be the same or different, are each a hydrogen atom or an alkyl radical having at most 4 carbons; x and y, which may be the same or different, are each an integer of 0 or 1, with the proviso that x+y is at least equal to 1; and Ar is a deactivated aromatic ring, preferably derived from formula (I) by replacement of R.sub.1 with a dialkylamine.

Dependencies are inferred from the claim text.