A surprising synthesis of 3-acetyl-6-chloro-2-methyl-4-phenylquinoline has been attained through convenient and efficient one-pot condensation of 3-chlorobenzophenone and acetylacetone. Its structure was elucidated by spectral data, X-ray diffraction studies and also investigated using density functional theory (DFT). Optimized geometry was obtained by performing DFT calculations at B3LYP level of theory and 6311+G (d,p) basis set. Frontier molecular orbital analysis has been executed at B3LYP/6-311+G(d,p) level of theory. The global reactivity parameters were explored using the energy of frontier molecular orbitals. Natural bond orbital analysis has been carried out at B3LYP/6-311+G(d,p) level of theory to discover hyper conjugative interaction and stability of the title molecule. Moreover, the product showed the reverse urease inhibition activity.