Hydrochloric Acid → HCID 90011309, compound

Participants

Reaction Conditions

Reaction Steps

(6-Bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester (10.9 g, 37.5 mmol) was dissolved in methanol (90 mL). Concentrated HCl (10 mL) was then added followed by iron (6.4 g, 110 mmol). The reaction mixture was stirred at 60° C. for 1 hour. Then, the reaction mixture was cooled to room temperature and neutralized with solid sodium bicarbonate. The insoluble iron salts were removed by centrifugation. Silica gel was then added to the supernatant and the solvents were removed under reduced pressure. The resulting crude material was purified by column chromatography (SiO2, EtOAc/hexanes) to give (2-amino-6-bromopyridin-3-yloxy)acetic acid methyl ester. Yield 4.0 g (15 mmol, 40%). LCMS (ESI): calc. C8H9BrN2O3=260, 262; obs. M+H=261, 263.

Provenance & Evidence