Methylamine → 4-chloro-N-methylpyridine-3-carboxamide

To a suspension of crude 4-chloronicotinoyl chloride hydrochloride in 25 mL of THF was added methylamine solution (2M in THF, 20 mL, 40 mmol, 4.0 eq) at 0° C. The reaction mixture was stirred at room temperature for 1 hour and concentrated under reduced pressure. The crude material was dissolved in ethylacetate (75 mL) and water/brine/saturated sodium bicarbonate solution (1/1/1, 75 mL). The separated aqueous layer was extracted with EtOAc. The combined organic layers were washed with water/brine/saturated sodium bicarbonate solution (1/1/1, 25 mL) and brine (25 mL) and dried over sodium sulfate. Removal of the solvent under reduced pressure afforded the title compound as orange solid (400 mg, 24%), which was used without further purification. MH+=171.0, Rt=0.55 min.

1. concentrationconcentrated under reduced pressure
2. dissolutionThe crude material was dissolved in ethylacetate (75 mL)
3. extractionThe separated aqueous layer was extracted with EtOAc
4. washThe combined organic layers were washed with water/brine/saturated sodium bicarbonate solution (1/1/1, 25 mL) and brine (25 mL)
5. dry with materialdried over sodium sulfate
6. customRemoval of the solvent under reduced pressure

ORD record

ord-b37186019860442ea635dff2cef4513f

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07553854B2