Hydrochloric Acid → Methyl 3-[(5-aminopyridin-2-yl)oxy]-4-methoxybenzoate

Participants

Reaction Steps

To a solution of methyl 4-methoxy-3-[(5-nitropyridin-2-yl)oxy]benzoate (26.7 mmol) in ethanol (250 mL) were added iron powder (5.6 g, 0.1 mol) and 6N hydrochloric acid (50 mL) with heating under reflux and vigorous stirring, and the mixture was vigorously stirred under refluxing condition for 1.5 hr. The reaction solution was filtered through celite, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate (350 mL), and washed with 1N aqueous sodium hydroxide solution (200 mL×2). The aqueous layer was extracted with ethyl acetate (150 mL×3), and the combined organic layer was washed with saturated aqueous ammonium chloride solution (100 mL×2), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated to give the title compound (8.0 g) as a brownish-red syrup substance.

Provenance & Evidence