Anthranilic Acid → HCID 22320187, compound

Participants

Reaction Steps

To a solution in a mixture of benzene (100 mL)/acetone (100 mL) of the crude 5-(2-hydroxybutylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione which was previously prepared from Meldrum's acid (57.7 g, 0.40 mol) and propionyl chloride(37.0 g, 0.40 mol) according to the methods described in Synthesis, p. 1213 (1992) and Org. Synth., vol. 63, p. 198 (1985), anthranilic acid (45.8 g, 0.33 mol) was added and the mixture was heated under reflux for 3 hours. The solution was cooled to room temperature and concentrated under reduced pressure. The residue was suspended in a mixture of acetic anhydride (68.1 g, 0.667 mol) and tetrahydrofuran (150 mL), and the suspension was heated under reflux for 30 minutes. The solution was cooled to room temperature and concentrated under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography (ethyl acetate:hexane=2:8) to give the title compound (28.4 g, 33% yield).

Provenance & Evidence