PURPOSE: To obtain an indoaniline dye simply and inexpensively, by oxidatively condensing a specified phenol or naphthol derivative with a p-phenylenediamine in the presence of either iodine or iodine and an alkali metal iodide.

CONSTITUTION: A compd. of formula I (e.g., 2-phenylcarbamoyl-1-naphthol) is oxidatively condensed with a r-phenylenediamine of formula II in the presence of either iodine or iodine and an alkali metal iodide to obtain an indoaniline dye of formula III. In the formulas, R1 and R2 are each H or an alkyl or R1 and R2 may be combined together to form a six-membered carbon ring; R3 is sulfo, carboxy etc.; R4 and R5 are each an alkyl or an aralkyl; R6 is H, an alkyl, an alkoxy or sulfo; X is an atom or a group which can be removed when bonded to the p-phenylenediamine of formula II.