GB1350229A - Indazolone derivatives their preparation and use as colour couplers - Google Patents

Abstract

1350229 Gadazolone derivatives and their preparation AGFA-GEVAERT AG 29 Dec 1971 [29 Dec 1970] 60404/71 Heading C2C [Also in Division G2] Compounds of the formula wherein R is hydrogen or C 1-3 alkyl, R 1 is hydrogen or alkyl, R 2 is alkyl containing up to 17 carbon atoms, and R 1 and R 2 may, together with the carbon atom joining them, form a cycloalkane ring, X and Y may be the same or different and represent hydrogen, halogen, C 1-18 alkyl, cycloalkyl, C 1-18 alkoxy, C 1-18 thioalkyl, phenyl, aryloxy or acylamino, and where the said groups may carry additional substituents, and X or Y may form, together with R 1 or R 2 and the carbon atoms joining them, a cycloalkene ring, and Z is hydrogen, sulphanyl, which may be substituted with monoalkyl, dialkyl or aryl groups, or a group which renders the compound soluble in alkali, may be prepared by reacting a suitably substituted styrene, optionally in the diameric form, or the corresponding α-carbinol, with an anthranilic ester in the presence of an acid catalyst to alkylate said ester in the 5-position, and effecting subsequent indazolone ring closure by a known method; the product may then be optionally sulphonated. The radicals X or Y, when an acylamino group, may be derived from aliphatic or aromatic carboxylic or sulphonic acids, the additional substituents may be, for example, halogen, hydroxyl, carboxyl, acylamino or carbonyl groups, and groups representative of Z which render the compounds soluble in alkali may be, for example, carboxyl or sulphonic, optionally in the anionic form. In examples: (1) dimeric isopropenyl phenol is reacted with potassium hydroxide and cetyl bromide to form the corresponding di-p-cetoxy ether, the latter is reacted with methyl anthranilate to form 5-[2- (4<SP>1</SP> - hexadecyloxyphenyl) - isopropyl] - anthranilic acid methyl ester which is diazotised and cyolised to give 5-[α-(4<SP>1</SP>-hexadecyloxy)-isopropyl] - indazolone which is then sulphonated in the 31-position; (2) o-hydroxy-acetophenone is etherified with cetyl bromide and the ketone group subsequently reduced to form o-cetoxy phenyl methyl carbinol, the latter is reacted with methyl anthranilate to form 5-[α-(2<SP>1</SP>- hexadecyloxyphenyl) - ethyl] - anthranilic acid methyl ester and indazolone ring closure is effected as above. The compounds of the above formula may be used as magenta forming couplers in light-sensitive photographic materials.