Potassium Hydroxide → 2-Carboxy-7-methyl-4-chloroquinoline

Participants

Reaction Conditions

Reaction Steps

To 20 mL POCl3 was added 2-carboxy-7-methyl-4-hydroxyquinoline (2.5 g, 12.3 mmol) and PCl5 (11.5 g, 55 mmol). The mixture was heated to 130° C. for 3 hours. The reaction mixture was cooled and poured onto ice. The solution was neutralized with solid NaOH and adjusted to pH 11 with solid KOH. The tan precipitate was filtered, slurried in 250 mL water and adjusted to pH 2 with concentrated HCl. The resultant solid was filtered and dried to afford 2-carboxy-7-methyl-4-chloroquinoline (1.34 g, 50%).

Provenance & Evidence