A novel Schiff base ligand 3-(2-(4-hydroxy-3-methoxy benzylidene) hydrazinyl)-2H-benzo[b] [1,4]oxazin-2-one (HMB-HBO) was synthesized from Hydrazino benzoxazine and Vanillin and characterized by elemental analysis, IR, 1H-NMR, LC-MS mass, electron absorption spectra and powder X-ray diffraction. 3D molecular modeling structure of the ligand was obtained by using Argus lab software. The Schiff base HMB-HBO is expected to behave as a multidentate chelating ligand, which can coordinate with the deprotonated phenolic oxygen, carbonyl oxygen and azomethine nitrogen atoms with different metals forming stable polymeric complexes possessing various biological activities.