One-pot synthesis of pyrazolotriazole photographic dye forming color couplers and coupler intermediates
AssigneeEastman Kodak Company
InventorsRonald R. Valente, Judith A. Bose
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AssigneeEastman Kodak Company
InventorsRonald R. Valente, Judith A. Bose
Estimating the term…
Photographic pyrazolotriazole dye forming coupler compounds of coupler intermediate compounds can be readily prepared in a single reaction medium by reacting certain pyrazolotriazole compounds with nitro-substituted aromatic compounds in the presence of a formate salt and a transition metal catalyst. This salt hydrogenates the nitro group and the carbonate by-product induces reaction of the resulting amine with the pyrazolotriazole compound. Yields and purity are high, and reaction time is reduced with the specific set of conditions and reactants, and environmental impact from waste is reduced. In addition, isolation of aromatic amine intermediates is avoided. The resulting pyrazolotriazole compounds can be used themselves as photographic dye forming couplers or further reacted to prepare useful coupler compounds for photographic use.
A method for preparing a pyrazolotriazole dye forming coupler compound or coupler intermediate compound of Structure I in a single reaction medium containing a transition metal catalyst, said method comprising reacting a nitro-substituted aromatic compound NO.sub.2 --Ar with a compound of Structure IV in the presence of a formatic salt ##STR39## wherein Ar is an aromatic group, R.sub.1 is an alkyl, aryl, alkoxy, aryloxy, acyl or amido group, R.sub.2 is hydrogen or an alkyl or aryl group, X is hydrogen or a coupling-off group or a precursor thereof, and Y is a leaving group that is capable of being replaced in an elimination-addition reaction,
Dependencies are inferred from the claim text.