GB914613A - New isoindoline derivatives and process for producing same - Google Patents

Abstract

The invention comprises isoindoline derivatives of the general formula <FORM:0914613/IV (b)/1> wherein Hal represents a halogen atom, R1 represents hydrogen or an alkyl group, and R2 represents an alkoxy or alkylamino group, a dialkylamino group the two alkyl groups of which may be joined together to form a 5- or 6-membered ring, or a dialkylamino-alkylamino group, and the preparation thereof by treating an isoindoline of the general formula <FORM:0914613/IV (b)/2> wherein Hal and R1 have the above significance, either direct or after treatment with an inorganic acid chloride or bromide to convert it into an isoindoline of the general formula <FORM:0914613/IV (b)/3> wherein Y represents chlorine or bromine, with a compound of the formula R2H, wherein R2 has the above significance, if necessary in the presence of an agent splitting off water such as thionyl chloride, phosphorus pentachloride or phosphorus tribromide, or an acid binding agent such as pyridine, trimethylamine or potassium carbonate. Substituted isoindolines of the general formula <FORM:0914613/IV (b)/4> wherein R1 and Hal have the above significance, are prepared by reacting compounds of the general formula <FORM:0914613/IV (b)/5> wherein Hal, R1 and Y have the above significance, with ammonia-preferably in the presence of an acid binding agent such as excess amine or ammonia. Substituted isoindolines of the general formula <FORM:0914613/IV (b)/6> wherein Hal and Y have the above significance, are prepared in the case wherein R1 is alkyl by reacting compounds of the general formula <FORM:0914613/IV (b)/7> wherein Hal and Y have the above significance, with amines of the general formula R1NH2 wherein R1 represents alkyl, and in the case wherein R1 represents hydrogen, by reacting compounds of the general formula <FORM:0914613/IV (b)/8> wherein Hal and Y have the above significance, with ammonia. Halogen substituted compounds of the general formulae <FORM:0914613/IV (b)/9> wherein R1, Hal and Y have the above significance, are prepared by condensing according to Friedel Crafts the required Hal substituted benzenes and phthalic acid anhydride or phthalic acid ester halides to form 41-halogen2-carboxybenzophenones or esters thereof, nitrating either of these compounds to form 41 - halogeno-31-nitro-2-carboxybenzophenones, reducing these phenones to form 41-halogeno-31-amino-2-carboxyphenones, diazotising the 31-amino compounds and decomposing the diazonium halides with sulphur dioxide in the presence of a copper salt such as cupric chloride or bromide to form 41-halogeno-31halogenosulphonyl-2-carboxy - benzophenones, reacting these compounds with ammonia to form 41 - halogeno-31-sulphamyl-2-carboxyphenones and treating these compounds with a hydrogen halide to form the 31-sulphamyl substituted lactones of the first general formula immediately above; and by treating the 41halogeno - 31 - halogeno-sulphamyl-2-carboxybenzophenones referred to above with a mineral acid to form the 31-halogenosulphamyl substituted lactones of the second general formula immediately above, and by treating these lactones with one mol of R1NH2 wherein R1 is hydrogen or alkyl, to form the isoindolines of the third general formula immediately above.