Hydrochloric Acid → 5-cyano-6-ethoxy-3-nitropicolinic Acid

Participants

Reaction Steps

To a stirred solution of the compound prepared in Example 446 (0.61 g) in dioxane (10 mL) at ambient temperature was added of a 2 mol/L solution of 2-methyl-2-butene in tetrahydrofuran (8.4 mL). To the resulting stirred solution was added a solution of sodium chlorite (80%, 1.37 g) and sodium dihydrogen phosphate monohydrate (1.37 g) in water (8 mL). The resulting mixture was vigorously stirred at ambient temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (15 mL), and after stirring for 10 minutes, the mixture was transferred to a separatory funnel. The aqueous layer was acidified with 6M hydrochloric acid to pH 1.5, and then extracted with chloroform (20 mL). The organic layer was dried over sodium sulfate and concentrated to provide the title compound (0.16 g) with the following physical data.

Provenance & Evidence