Quinoline-quinone-(3, 4) diazide plates

专利名称：Quinoline-quinone-(3, 4) diazide plates发明人：SUS OSKAR,GLOS MARTIN申请号：US48456955申请日：19550127公开号：US2859112A公开日：19581104

摘要： Quinoline - 3 : 4 - quinone - 3 - diazides of the formula shown are prepared bycondensing anthranilic acid with nitro-acetaldoxime to give N - (b - nitroethylidene) -anthranilic acid, ring-closing the latter with acetic anhydride to 3-nitro-4-hydroxy-quinoline, reducing the nitro group to amino catalytically or with sodium dithionite(isolating the amine as hydrochloride), diazotizing with sodium nitrite and treating thediazonium chloride with alkali. The process is applicable to substituted derivatives(including those with condensed aromatic nuclei) and examples are given of theproduction of the following substituted quinone diazides and of the correspondingsubstituted intermediates: 7-methyl, 6 : 8-dimethoxy, 7-phenyl, 6-phenoxy, 6-chloro, 7-carbomethoxy, 6-sulphonic acid phenyl ester, 6-sulphon-n-butylamide, 6-sulphoncyclohexylamide, 6-sulphondimethylamide and 6 : 7-benzo. 7-Chloro-3 - amino - 4- hydroxy - quinoline and 2 : 4-dihydroxy-3-amino-quinoline which can also be convertedto the corresponding 3 : 4-quinone-3-diazides are made by nitration of 7-chloro-4-hydroxyquinoline and 2 : 4-dihydroxyquinoline respectively, reduction to amino andconversion to hydrochloride. The following (substituted anthranilic acids) are made byreduction of the corresponding nitro compounds: 3-aminodiphenyl-4-carboxylic acid, 4-amino-diphenylether-3-carboxylic acid, 3-carboxysulphanilic acid phenyl ester, 3 - carboxy

- N : N - dimethyl - sulphanilamide, 3 - carboxy - N - cyclohexyl - sulphanilamide and 3 -carboxy - N - butyl - sulphanilamide. They are mostly isolated as hydrochlorides. 3 -Nitrodiphenyl - 4 - carboxylic acid is obtained by hydrolysis of its nitrile. 4 - Nitrile -diphenylether - 3 - carboxylic acid is prepared by condensing phenol with 2-nitro-5-chlorobenzoic acid. 4 - Nitro - 3 - carboxy - benzenesulphonyl chloride is made bydiazotizing 2-nitro-5-aminobenzoic acid and passing in sulphur dioxide; this is reacted withphenol, dimethylamine, butylamine and cyclohexylamine to give the corresponding esterand amides.ALSO:Azo dyes are formed by coupling diazotized 3 - amino - 4 -hydroxyquinoline or its substitution derivatives with azo components; they form lakeswith metallic salts. Specified substituents are methyl, methoxy, phenyl, phenoxy, chloro,hydroxy, carbomethoxy, sulphonic acid phenyl esters and N - butyl, N - cyclohexyl andN:N - dimethyl - sulphonamide, and also condensed aromatic rings, e.g. 6:7-benzo.

申请人：AZOPLATE CORPORATION

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