Methylamine → 3-chloro-N-methylisonicotinamide

To a suspension of crude 3-chloroisonicotinoyl chloride hydrochloride in 25 mL of THF was added methylamine solution (2M in THF, 20 mL, 40 mmol, 8.4 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 EtOAc (75 mL) and water/brine/saturated sodium bicarbonate solution (1/1/1, 75 mL) and phase separated. The 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 an off-white solid (321 mg, 39.7%), which was used without further purification. ES/MS m/z 171.0, (MH+), Rt=0.65 min.

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

ORD record

ord-1cf31993b4d04441874f578d7305f484

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293769B2