Ammonia → 4-Chloropyridine-2-carboxamide

To a solution of 4-chloropicolinic acid (100 mg, 0.64 mmol) in DCM (10 mL) was added one drop DMF and SOCl2 (0.14 mL, 1.92 mmol). The reaction was stirred at rt overnight, then concentrated in vacuo. The resulted residue was dissolved in THF (10 mL), followed by the addition of Et3N (0.2 mL, 0.13 mmol). The mixture was stirred in an ammonia gas atmosphere for 1 hour, then concentrated in vacuo, diluted with water (20 mL) and extracted with ethyl acetate (10 mL×3). The combined organic phases were washed with brine (20 mL), dried over anhydrous Na2SO4, concentrated in vacuo and the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=5/1) to give the title compound as a yellow solid (70 mg 70%).

1. concentrationconcentrated in vacuo
2. dissolutionThe resulted residue was dissolved in THF (10 mL)
3. concentrationconcentrated in vacuo
4. additiondiluted with water (20 mL)
5. extractionextracted with ethyl acetate (10 mL×3)
6. washThe combined organic phases were washed with brine (20 mL)
7. dry with materialdried over anhydrous Na2SO4
8. concentrationconcentrated in vacuo
9. customthe residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=5/1)

ORD record

ord-edd0b6ff7463479e901b7edf78c41fbc

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09326975B2