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-fc3c852e39654da086ec0d15afd3286d

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710048B2