3-Hydroxy-2-naphthoic acid → 3-Hydroxynaphthalene-2-carbonyl chloride

Participants

Reaction Steps

The azo pigments of Formula II listed in FIG. 6 may be prepared, for example, by reacting 2-hydroxy-3-naphthoic acid with thionyl chloride to obtain 2-hydroxy-3-naphthoic acid chloride. Subsequently, the formed acid chloride is added to a solution of N,N-diethylaniline, and an appropriately substituted aniline to yield a coupler compound. A 5 millimole amount of 2,7-diaminodibenzothiophene sulfone is then tetrazotized by an excess amount of a metal nitrite such as sodium nitrite in hydrochloric acid at from about 0° C. to about 30° C., and the product is reacted with HBF4. An 11 millimole amount of the coupler compound previously prepared is then added to the resulting tetrazonium salt in a solution of dimethylformamide at from about 0° C. to about 30° C., followed by the addition of a base, such as sodium acetate in water, to the reaction mixture. The resulting precipitated product is a disazo pigment of Formula II, the specific compound obtained depending on the substituents present in the coupler compound. For example, 3,5-difluoroaniline is selected to obtain the coupler compound 2-hydroxy-3-naphtho-3',5'-difluoroanilide, which is then used to prepare 2,7-bis(1'-azo-2'-hydroxy-3'-naphtho-3",5"-difluoroanilide)dibenzothiophene sulfone. The azo pigments are isolated by filtration and purified by repetitive solvent washings, and may be characterized by elemental analysis, melting point, and IR spectroscopy.

Provenance & Evidence