Ciba-geigy Corporation

Franz Felix

Christoph Frey

Jean Indermuhle

Rudolf W Pfluger

3-Phenylpyrrole derivatives of formula I ##STR1## wherein X is cyano, --CO--R.sub.3, --CO--OR.sub.3 or ##STR2## R.sub.1 and R.sub.2 are each independently of the other hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, cyano, halogen or C.sub.1 -C.sub.6 haloalkyl, or R.sub.1 and R.sub.2, when taken together, are methylenedioxy or difluoromethylenedioxy, R.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl or benzyl, or phenyl or benzyl which are each substituted by halogen, methyl, methoxy or methylthio, and R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl or benzyl, or phenyl or benzyl which are each substituted by halogen, methyl, methoxy or methylthio, are prepared by (a) reacting N-(p-tolylsulfonyl)methyl formamide, in an inert solvent and in the presence of an organic base, with phosphoroxy chloride, mixing the reaction solution with water, separating the aqueous phase of the resultant two-phase mixture, and (b) reacting the organic phase containing (p-tolylsulfonyl)methyl isocyanide direct with a compound of formula II ##STR3## wherein X, R.sub.1 and R.sub.2 are as defined for formula I, Y is --CO--NHR.sub.4, --CO--R.sub.5 or --S--R.sub.5, R.sub.5 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl or benzyl, or phenyl or benzyl which are each substituted by halogen, methyl, methoxy or methylthio, and R.sub.4 is as defined for formula I, in the presence of a base.

Process for the preparation of 3-phenylpyrrole derivatives

Transition-metal complexes of hydrazones of the formula ##STR1## wherein A and B independently of one another are isocyclic or heterocyclic aromatic radicals and D is hydrogen, are suitable for pigmenting high-molecular organic material.

Use of metal complexes of hydrazones as pigments

1:2 Nickel or 1:2 copper complexes of a naphthostyril of the formula ##STR1## or of tautomers thereof, in which A, X and Y are as defined in claim 1, are suitable for pigmenting high molecular weight organic material.

Growing community of inventors

Munchenstein, Switzerland

Franz Felix