Methyl 5-chloro-2-[(5-nitropyridin-2-yl)oxy]benzoate → Methyl 2-[(5-aminopyridin-2-yl)oxy]-5-chlorobenzoate

Participants

Reaction Steps

A mixture of methyl 5-chloro-2-[(5-nitropyridin-2-yl)oxy]benzoate (step 1, 1.59 g, 5.2 mmol) and 5% palladium on activated carbon (149 mg) in ethyl acetate (25 mL) was stirred at room temperature for 1 h under hydrogen atmosphere. The reaction mixture was filtered through a pad of Celite® and the filtrate was evaporated. The residue was purified by flush column chromatography on silica gel eluting with dichloromethane/methanol (50/1) to afford 301 mg (21%) of the title compound: 1H-NMR (CDCl3) δ 7.92 (1H, d, J=2.8 Hz), 7.56 (1H, d, J=2.6 Hz), 7.47 (1H, dd, J=8.7, 2.6 Hz), 7.11 (1H, dd, J=8.6, 2.8 Hz), 7.08 (1H, d, J=8.7 Hz), 6.82 (1H, d, J=8.6 Hz), 3.74 (3H, s), 3.49 (2H, br.s).

Provenance & Evidence