Sodium Hydroxide → 2-[2-Fluoro-4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionic acid

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-[2-fluoro-4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionate (3.23 g; 8.27 mmole) was dissolved in a warm mixture of isopropanol (150 ml) and tetrahydrofuran (30 ml). The solution was allowed to cool to a temperature of 25° C. and a solution of sodium hydroxide (0.34 g) in water (10 ml) was added slowly with stirring. The reaction mixture was stirred at room temperature for a period of 10 minutes and then aqueous 2M sodium hydroxide (0.5 ml) was added and the solution was stirred at room temperature for 5 hours. The solvent was removed from the reaction mixture by evaporation under reduced pressure and the residue was dissolved in water. The aqueous solution was treated with aqueous 2M hydrochloric acid until acidic and the precipitated product was collected by filtration and air dried. The product was recrystallised from toluene to give the title compound (1.83 g; 61%), mp 132°-138° C. The assigned structure was confirmed by nuclear magnetic resonance spectroscopy.

Provenance & Evidence