Mannich Reaction Product of Quinolin-8-ol (Oxine) and its Antibacterial Activity

Quinolin-8-ol (1) on reaction with 2,6-dichloroaniline and m-nitrobenzaldehyde afforded 7-(α-hydroxy- m-nitrobenzyl)quinolin-8-ol (2), which is an unusual Mannich reaction product. The structure of (2) was determined by spectroscopic and single-crystal X-ray diffraction studies. Preliminary antimicrobial screening showed that (1) and (2) have activity against a large number of Gram-positive and Gram-negative bacteria.