Novel substituted 4-methyl-4,5-dihydropyrrolo[1,2-<i>a</i>]-quinolines were prepared by a simple two-step approach involving a Clauson-Kaas reaction of a substituted <i>ortho</i>-allylaniline followed by acid-catalyzed regioselective intramolecular Friedel–Crafts alkylation of the resulting 1-(2-allylaryl)-1<i>H</i>-pyrroles. All the synthetized compounds were fully characterized by IR, ¹H and ¹³C NMR spectroscopy, and mass spectrometry.