N-(4-hydroxyphenyl)acetamide (0.36 g, 2.4 mmol)), 2-chloro-8-methylquinoline-3-carbaldehyde (0.5 g, 2.4 mmol), potassium carbonate (0.67 g, 4.7 mmol), and 0.1 g moist copper powder were mixed to a 100 mL round-bottom flask in DMF (20 mL). An air condenser was fitted to the neck and refluxed for 5 hours until N-(4-hydroxyphenyl)acetamide completely disappeared on TLC analysis. Then, it was cooled to room temperature and poured to 100 mL crushed ice water. The precipitate was separated by suction filtration and washed with of 5% aqueous NAOH (50 mL) and air dried. The product was a gray powder, and the yield was 1.0 g (89%)
An aqueous solution of KOH (1 mL, 40%) was added dropwise to a mixture of N-(4-((3-formyl-8-methylquinolin-2-yl)methyl)phenyl)acetamide (0.94 g, 2.0 mmol) and benzyltriphenylphosphonium chloride (0.78 g, 2.0 mmol) dissolved in DMF (15 mL) in a 100 mL round-bottom flask while being stirred with a magnetic stirrer. The stirring was continued for 16 hours at which TLC analysis showed the complete conversion of the reactant. Then, the mixture was poured to 150 mL crushed ice water, and the precipitate was separated by suction filtration and washed with 30 mL cold water. The crude product was 0.99 g (91.1%)
2-Methoxy-8-methylquinoline-3-carbaldehyde (0.6 g, 3 mmol)) aluminum powder (0.16 g, 6 mmol) and potassium hydroxide (1.1 g, 18 mmol) were added to 10 mL methanol in a 100 ml round-bottom flask with an air condenser. The flask was mounted over a magnetic stirrer, and the reaction mixture was stirred for 12 hours. The progress of the reaction was monitored by TLC. The reaction mixture was filtered to remove unreacted aluminum powder, and 50 mL water was added to the filtrate. The precipitate was collected by suction filtration and air dried. The crude product was 0.53 g (43.7%)
