Ethanol → Ethyl 5-aminopyridine-2-carboxylate

To a solution of 5-aminopicolinic acid (13.5 g, 97.7 mmol) in anhydrous ethanol (200 mL) was added SOCl2 (60.0 mL, 504 mmol) dropwise at 0° C. under N2 atmosphere. The resulting mixture was heated at reflux and stirred overnight. The reaction mixture was concentrated in vacuo. The residue was dissolved in a saturated aqueous NaHCO3 solution so that that pH of the solution was approximately pH 9-10. The reaction mixture was extracted with EtOAc (8×250 mL). The combined organic phases were dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo to afford the title compound as a brown solid (14.3 g, 88%)

1. temperatureThe resulting mixture was heated
2. temperatureat reflux
3. concentrationThe reaction mixture was concentrated in vacuo
4. dissolutionThe residue was dissolved in a saturated aqueous NaHCO3 solution so that that pH of the solution
5. extractionThe reaction mixture was extracted with EtOAc (8×250 mL)
6. dry with materialThe combined organic phases were dried over Na2SO4
7. filtrationfiltered
8. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-7c959703e32648098e41208d0fac21c9

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227956B2