4-Methoxyphenylacetic Acid → 2-(4-methoxyphenyl)-N-pyridin-2-ylacetamide

Participants

Reaction Steps

To a solution of 4-methoxyphenyl acetic acid (5 g; 30.08 mmol) in 30 ml of dichloromethane, under nitrogen, it was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (6.34 g; 33.09 mmol) in small portions. After 10 minutes 2-aminopyridine (2.83 g; 30.08 mmol) was added and stirred for 4 hours at rt. The reaction mixture was concentrated and partitioned between ethyl acetate and 0.5N HCl. The organic phase was washed with 0.5N HCl (2×) and 0.5N NaOH (2×). The pH of the acidic/aqueous phase was adjusted to ˜7 with 0.5N NaOH and extracted twice with ethyl acetate. The basic/aqueous phase was also extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated to afford 2-(4-methoxyphenyl)-N-pyridin-2-ylacetamide (7 g; 92% yield), which was used in the next step without further purification. MS: m/z 243 (M+1).

Provenance & Evidence