Ethanol → Ethyl 6-Aminopyridine-2-carboxylate

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).

1. customThe resulting reaction mixture
2. temperatureat reflux for 12 h
3. concentrationthe reaction mixture was concentrated under reduced pressure
4. additionSaturated aqueous Na2CO3 solution was added until the pH of the solution
5. concentrationThe mixture was concentrated under reduced pressure and dichloromethane (150 mL)
6. additionwas added to the resulting residue
7. stirringThe mixture was stirred vigorously at room temperature for 30 min
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-b03f203d23984fe6a03457fd969a5e0a

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987258B2