Ethanol → ethyl 6-aminopicolinate

To a solution of 2-amino-6-pyridinecarboxylic acid (90; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0° C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH=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 ethyl 6-aminopicolinate 91 (5.5 g, 76%).

1. customThe resulting reaction mixture
2. temperatureunder reflux for 12 h
3. concentrationthe reaction mixture was concentrated under reduced pressure
4. additionEnough saturated aqueous Na2CO3 solution was added
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-8ee77b3e922e4834a1d2d24487d466e6

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846947B2