A novel approach was adopted for the synthesis of series of Knoevenagel condensation products from 5-chloro-3-methyl-1-phenylpyrazole-4-carboxaldehyde with different cyclic active methylene compounds, using water soluble and recyclable Zn(Proline)2 as a Lewis acid catalyst both under solvent-free condition and using water as a reaction medium in good yields. In each conversion, the catalyst was successfully recovered and recycled without significant loss in yield and selectivity. The compounds were screened for their antimicrobial activity.