Hydrochloric Acid → HCID 67328970, compound

Participants

Reaction Steps

To an EtOH (500 mL) solution of butyl (E)-3-{3-chloro-4-[(5-nitropyridin-2-yl)oxy]phenyl}prop-2-enoate (45.4 g) and tin powder (57.3 g) was slowly added conc. HCl (36.6 mL) at 0° C., then the resultant mixture was stirred at room temperature for 1 hour. The reaction mixture was neutralized with 5 M aqueous NaOH, and the mixture was filtered off on Celite. The filtrate was evaporated and water was added to the residue, and the mixture was extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1) to afford butyl (E)-3-{4-[(5-amino-pyridin-2-yl)oxy]-3-chlorophenyl}prop-2-enoate (39.9 g) as a pale yellow solid.

Provenance & Evidence