ES416721A1 - Procedure for the production of azoic compounds of low solubility. (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

Procedure for the production of azo compounds of low solubility, of the formula: **(See formula)** wherein R1 signifies a hydrogen atom or a nitro group, R2 signifies a hydrogen, chlorine or bromine atom, a nitro, alkyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, phenyl or benzoyl radical or a substituted phenyl or benzoyl radical of up to three substituents selected from chlorine and bromine atoms, cyano or nitro groups, the alkyl radicals and the alkyl and alkoxy moieties containing in such radicals having 1 to 4 carbon atoms, meaning a chlorine or bromine atom, a cyano, nitro, alkoxycarbonyl, alkyl carbonyloxy, benzoyloxy or phenoxycarbonyl radical or a benzoyloxy or phenoxycarbonyl radical substituted by up to three substituents selected from chlorine and bromine atoms, cyano and nitro groups, containing the alkyl and alkoxy moieties in the said radicals of 1 to 4 carbon atoms, or R2 and R3 together signify a radical corresponding to the formula -CH = CH-CH = CH-, unsubstituted or substituted by up to three substituents selected from chlorine and bromine atoms, cyano and nitro groups, and X means a radical 1- (β-alkoxycarbonyl-alkylamino) -naphthyl, 1- (β-acetoxyalkylamino) -naphthyl, 2- β-alkoxycarbonyl-alkylaminoanisyl or a 3-β-alkoxycarbonylalkylamino-chlorobenzyl radical, the alkyl and alkoxy moieties containing said radicals of 1 to 4 carbon atoms, or a radical of formulas II, III, VIII or IX, **(See formula)** wherein R4 and R5, which may be the same or different, each mean a hydrogen atom, an unsubstituted alkyl radical or an alkyl radical substituted by up to two substituents selected from chlorine and bromine atoms, hydroxy radicals, cyano, alkoxy, phenoxy, alkanoyl, alkanoyloxy, chloroalkanoyloxy, benzoyloxy, alkoxycarbonyl, alkoxycarbonyloxy, alkylaminocarbonyl, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, phenylaminocarbonyloxy, pyridyl and **(See formula)** said alkyl radicals containing alkoxy substituents and alkyl and alkoxy moieties containing in such substituents of 1 to 4 carbon atoms, and containing the alkanoyl substituents and the alkanoyl moieties in such substituents of 1 to 5 carbon atoms, with the requirement that when one of the symbols R4 and R5 signifies a hydrogen atom, the other must have a different meaning from that of hydrogen, R6 signifies a hydrogen, chlorine or bromine atom, a cyano, alkyl, formylamino, alkylsulfonylamino, benzoylamino radical, alkylcarbonylamino, alkoxycarbonylamino, cyanoacetylamino, chloro- or bromoalkylcarbonylamino or alkoxyalkoxycarbonylamino, the said alkyl radicals and the alkyl and alkoxy moieties containing said radicals having 1 to 4 carbon atoms, R7 signifying a hydrogen atom or an alkoxy radical of 1 to 4 carbon atoms, R8 means a hydrogen atom, an alkylamino, dialkylamino or phenylamino radical, an unsubstituted alkyl radical ir or an alkyl radical substituted by a hydroxy, cyano, alkoxy, alkanoyloxy or phenyl radical, said alkyl radicals and moieties containing the alkoxy substituents on such radicals having 1 to 4 carbon atoms and the alkanoyl moieties containing on such substituents of 1 to 5 carbon atoms, R9 means a cyano group or an alkylsulfonyl radical, containing from 1 to 4 carbon atoms, R10 means an alkyl radical of 1 to 4 carbon atoms or a phenyl radical, said compounds being free of water-solubilizing groups ; characterized in that an amine of formula IV is diazotized, **(See formula)** wherein R1, R2, and R3 are as defined above, and then the resulting diazonium compound is coupled with a compound of formula V, **(See formula)** where K is as defined above. (Machine-translation by Google Translate, not legally binding)