Hydrochloric Acid → HCID 22929687, compound

Participants

Reaction Steps

After dissolving the methyl 5-bromo-2-(dimethylamino)-4-(hydroxymethyl)benzoate (1.179 g, 4.1 mmol) in a tetrahydrofuran (10 ml)-methanol (10 ml) mixed solvent, a 1 N sodium hydroxide aqueous solution (9.8 ml, 9.8 mmol) was added and the mixture was heated to reflux for 4 hours. Next, 5 N hydrochloric acid (9.8 ml, 9.8 mmol) was added and the reaction mixture was concentrated under reduced pressure. Acetonitrile was added to the residue and the mixture was concentrated under reduced pressure, and then the same procedure was repeated twice. Acetonitrile (20 ml), a 2.0 M dimethylamine-tetrahydrofuran solution (4.1 ml, 8.2 mmol), 1-hydroxybenztriazole (1.11 g, 8.2 mmol) and dicyclohexylcarbodiimide (1.69 g, 8.2 mmol) were added to the residue in that order and the mixture was stirred at room temperature for 20 hours. The insoluble portion was filtered off, the reaction mixture was concentrated under reduced pressure, ethyl acetate was added and the mixture was filtered through alumina. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1.222 g) as a white solid. (100% yield)

Provenance & Evidence