Synthesis, Molecular Docking Analysis, and Evaluation of Antibacterial and Antioxidant Properties of Stilbenes and Pinacol of Quinolines
Table 3
Continued table of the synthesized compounds and their synthetic procedure.
No
Synthesized compound
Synthetic procedure
7
(Z)-2-methoxy-3-styrylquinoline (9)
An aqueous solution of KOH (1 mL, 40%) was added dropwise to a mixture of 2-methoxyquinoline-3-carbaldehyde (0.50 g, 2.6 mmol) and benzyltriphenylphosphonium chloride (1.01 g, 2.6 mmol) dissolved in 10 mL DMF in a 100 mL round-bottom flask while being stirred with a magnetic stirrer. The stirring was continued for 8 hrs at which TLC analysis showed the complete consumption of the reactant. Then, the mixture was poured into 100 mL crushed ice water, and the precipitate was collected with suction filtration. The crude product was 0.6 g, (88%); mp 138–140°C
2-Chloroquiomoline-3-carbaldehyde (0.5 g, 2.6 mmol) was added to 10 mL 2-aminoethan-1-ol in a 100 mL round-bottom flask and heated to 90–95°C for an hour in a water bath. The completion of the reaction was monitored by TLC. The resulting mixture was cooled to room temperature and added to 100 mL cold ice water. The precipitate was separated by suction filtration and washed with 20 mL cold water. The product was a yellow powder, and the yield was 0.59 g (84%); mp 80–82°C
9
2-Chloro-8-methylquinoline-3-carbaldehyde (13)
The synthesis 2-chloro-8-methylquinoline-3-carbaldehyde was carried out with the procedure discussed above for the synthesis of 2-chloroquinoline-3-carbaldehyde, by replacing acetanilide with 2-methylacetanilide (21 g, 0.14 mol). The crude product was a yellow powder, and the yield was 17.94 g (62.3%)
