In recent years, the chemistry of 2-chloroquinoline-3-carbaldehydeshave received considerable attention owing to their synthetic and effective biological importance which exhibits a wide variety of biological activity, and 2-chloro- 3-((2,2-dimethylhydrazono)methyl)quinoline derivatives that synthesized from 2-chloroquinoline-3-carbaldehydes may have biological effects as non-nucleoside Human HIV-1 Reverse Transcriptase Inhibitors. A group of 2-chloro- 3-((2,2-dimethylhydrazono)methyl) quinolone derivatives were synthesized, and theoretically evaluated for their inhibitory as non-nucleoside Human HIV-1 Reverse Transcriptase Inhibitors via docking process. The docking calculation was done in GOLD 5.2.2 software using Genetic algorithm. Compounds3g and 3b showed the best inhibitory potency by GOLD score value of 79.24 and 78.34 respectively. Some of the best models formed strong hydrogen bonds with Lys 103via quinoline moiety. It was found that pi-pi interaction between Lys 103,Lys 101, Trp229, Trp 181, Tyr 181, Tyr 188, and Phe 227 side chain and quinolin moiety was one of the common factors in enzyme-inhibitor junction. It was found that both hydrogen bonding and hydrophobic interactions are important in the structure and function of biological molecules, especially for inhibition in a complex.