A series of new dyes based on the N-analogue of Pechmann hybrid dyes were prepared by the condensation of different 5-aryl derivatives of pyrrolinone ester (phenyl, 4-bromophenyl, thienyl, and biphenyl) with isatin. N-Alkylated derivatives were also prepared using bromoethyl acetate. Full 1 H and 13 C NMR assignment was performed. All prepared dyes were soluble in most organic solvents: N-alkylated derivatives had better solubility than non-alkylated derivatives. The UV-vis absorption spectra of the derivatives under study are quite similar and exhibit maxima in the 509-526 nm range. No E/Z photoisomerisation is observed. The dyeing process, dye exhaustion on polyester, and the fastness properties of the dyes were examined.