Triethylamine → 2-Chloro-N-methoxy-N-methylnicotinamide

2-Chloro-nicotinic acid (10.0 g, 63.5 mmol, 1.0 equiv) is suspended in dichloromethane (400 mL) and THF (100 mL). N,O-Dimethyl-hydroxylamine hydrochloride (6.81 g, 69.8 mmol, 1.1 equiv) and triethylamine (9.70 mL, 69.8 mmol, 1.1 equiv) are added, resulting in a clear solution. The mixture is cooled in an ice bath and EDCI (13.4 g, 69.8 mmol, 1.1 equiv) and HOAt (0.86 g, 6.35 mmol, 0.1 equiv) are added. The resulting mixture is stirred overnight at room temperature and concentrated in vacuo. The residue is redissolved in ethyl acetate (200 mL) and washed with 1N NaOH solution, twice with sat. NaHCO3 solution and brine. The organic phase is dried over Na2SO4, filtered and concentrated in vacuo. This gives 7.53 g of the title compound as a white solid. Yield: 59%

1. customresulting in a clear solution
2. temperatureThe mixture is cooled in an ice bath
3. concentrationconcentrated in vacuo
4. dissolutionThe residue is redissolved in ethyl acetate (200 mL)
5. washwashed with 1N NaOH solution, twice with sat. NaHCO3 solution and brine
6. dry with materialThe organic phase is dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-301b60795c224796b1fab9484c729b44

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985753B2