Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1981-03-16
1983-12-27
Torrence, Dolph H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
2604299, 544103, C07D20982, C07F 306
Patent
active
044232268
ABSTRACT:
Zinc chloride complex compounds to which the structure of the general formula (1) ##STR1## can be assigned, in which the individual radicals in the formula have the following meanings: Rhu 1 is a hydrogen atom or an optionally substituted lower alkyl group; R.sup.2 is a hydrogen atom, an optionally substituted lower alkyl group or an optionally substituted phenyl radical; R.sup.3 is a hydrogen atom or an optionally substituted lower alkyl group; R.sup.4 is a hydrogen atom, an optionally substituted lower alkyl group or an optionally substituted phenyl radical; R.sup.5 is a hydrogen atom or a halogen atom or a lower alkyl group or a lower alkoxy group, or R.sup.1 and R.sup.5 together form the o-phenylene radical; R.sup.6 is a hydrogen atom or a halogen atom or a lower alkyl group or a lower alkoxy group; Z is a hydrogen atom or a halogen atom or a lower alkyl group or a cyano, carboxylic acid, carbamoyl or sulfamoyl group or a carbamoyl or sulfamoyl group which is monosubstituted or disubstituted by lower alkyl, or a trifluoromethyl or lower carbalkoxy group, a lower alkoxy group which can be substituted by cyano, an acyloxy group, an acylamino group, a lower alkylamino group or a lower dialkylamino group. They are prepared by reacting a nitroso compound of the formula (2) ##STR2## in which R.sup.3, R.sup.4, R.sup.6 and Z have the meanings mentioned above, with an m-aminophenol of the formula (3) ##STR3## in which R.sup.1, R.sup.2 and R.sup.5 have the meanings mentioned above, in the presence of zinc chloride and in the absence of a base. The zinc chloride complex compounds of the formula (1) can be converted by eliminating the radical Z in the formula or by removing, by oxidative means, this radical Z, in the formula, which is in the ortho-position in relation to the nitrogen atom, or the other hydrogen atom which is in the ortho-position, into the phenoxazine dyestuffs of the formula (4) ##STR4## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the meanings mentioned above and Z.sub.1 denotes a halogen atom, a lower alkyl group, a cyano, carboxylic acid, carbamoyl or sulfamoyl group, a carbamoyl or sulfamoyl group which is monosubstituted or disubstituted by lower alkyl, or a trifluoromethyl or lower carbalkoxy group or a hydrogen atom and X.sup.(-) represents and anion.
REFERENCES:
patent: 3894012 (1975-07-01), Baumann et al.
Chem. Abs. 79:5096b (1973).
Ullmanns Encyklopaedie der Technischen Chemie, 4th edition, vol. 8, Verlag Chemie, 1974, pp. 224 and 234-237.
Ullmanns Encyklopaedie der Technischen Chemie, 3rd edition, vol. 13, Urban & Schwarzenberg, 1962, pp. 56 and 57.
Mohr Reinhard
Neeb Rudolf
Hoechst Aktiengesellschaft
Torrence Dolph H.
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