Abstract: A method to make squaraine dyes involves the reaction of 1,8-diaminonaphthalene with 1,3-dihydroxyacetone dimer in a first reaction mixture comprising the appropriate solvents to prepare a first intermediate. This first intermediate is then reacted with an organic acylating agent in the presence of a suitable solvent to form a second intermediate. Lastly, after isolation, the second intermediate is reacted with squaric acid in a particular hydroxylic solvent/nonpolar solvent mixture that dissolves squaric acid and forms a ternary azeotrope with water and the water is at least partially removed. The resulting dyes have the following general structure wherein R is an organic radical derived from the organic acylating agent.

Abstract: Phenolic cyan-dye-forming couplers characterized by a p-cyanophenylureido group in the 2-position of the phenol are synthesized in high yield by a process comprising the steps of contacting, in a reaction solvent in the presence of a transition metal catalyst at moderate temperature and atmospheric pressure, a coupler intermediate having a nitro group in the 5-position with a hydrogen donor, such as, for example, ammonium formate, to thereby form the corresponding 2-(p-cyanophenylureido)-5-aminophenol and reacting the 2-(p-cyanophenylureido)-5-aminophenol with an acylating agent to form the phenolic cyan-dye-forming coupler.