2-Hydroxy-1, 4-naphthoquinone, 3-nitro-, 3-chloro-, 3, 5-(or 3, 8) dinitro-, 3-chloro-5 (or 8) nitro-2-hydroxy-1, 4-naphthoquinone were synthesized from 1, 4-naphthoquinone, these were reacted with phenylhydrazine and 2, 4-dinitrophenylhydrazine, respectively, and ten kinds of 1-phenylazo-2, 4-dihydroxynaphthalene derivatives were synthesized. Dyeing properties of these products for acetate, Vinylon and Amylan were studied. In general, they showed clearness of coloration but that prepared by coupling with 2, 4-dinitrophenydrazine was slightly inferior in dyeing ability. Resistance to sunlight was not good with the exception of several Vinylon dyeings.