Ethanol → Ethyl 6-Aminopyridine-2-carboxylate

Participants

Reaction Steps

To a solution of 2-amino-6-pyridinecarboxylic acid 77 (6.0 g, 43.5 mmol) in ethanol (150 mL) was added thionyl chloride (12.0 g, 101 mmol) at 0° C. The resulting reaction mixture was stirred at reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Saturated aqueous Na2CO3 solution was added until the pH of the solution reached 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford 78 (5.5 g, 76% yield).

Provenance & Evidence