IE38498L - Substituted benzamides - Google Patents

Abstract

1427377 N - (Aminoalkyl) - benzamides SOC D'ETUDES SCIENTIFIQUES ET INDUSTRIELLES DE L'ILE - DEFRANCE 8 Nov 1973 [9 Nov 1972] 51888/73 Heading C2C Compounds IV in which R 1 is H or alkyl, R 2 is NH 2 , NO 2 , benzylamino tritylamino or acylamino, R 3 and R 4 are H or alkyl, W is alkylene and X is H or halogen are prepared by reacting compound II in which COY represents a carboxyl group or a reactive derivative thereof with an amine R 5 R 6 C=N-W-NR 3 R 4 (in which R 5 and R 6 are each a residue of a carboxylic acid from which the terminal carboxyl group is removed) to form a novel intermediate III in which A represents or or an isomer thereof which is hydrolysed. Compounds IV (R 2 is other than NH 2 ) are converted to compound IV (R 2 =NH 2 ) by hydrogenation or hydrolysis. Compounds IV prepared are those in which R 1 is methyl, R 3 and R 4 are ethyl, W is ethylene, X is chlorine and R 2 is nitro, amino, acetylamino or benzylamino. N- (2 - diethylaminoethyl) - 2 - methoxy - 4 - aminobenzamide is also prepared and is chlorinated to give the corresponding 5-chloro compound. N - (4 - Oxo - 2 - butylidene); N - (benzylidene)- N - (2 - hydroxy - benzylidene)- and N - (1- carbethoxyethylidene)- N<SP>1</SP>,N<SP>1</SP> - diethyl - ethylenediamine are prepared by reacting N,N-diethylethylenediamine with the appropriate ketone. [GB1427377A]