Methyl iodide → 3-chloro-1-methyl-5-nitropyridin-2(1H)-one

To a stirred suspension of 3-chloro-2-hydroxy-5-nitropyridine (25 g, 143 mmol) and K2CO3 (39.6 g, 286 mmol) in DMF (250 ml) under Ar, MeI (13.43 ml, 215 mmol) was added at 0° C. and the reaction mixture was stirred 3 hours at RT. The reaction mixture was concentrated, diluted with 300 ml water and extracted twice with 400 ml EtOAc. The combined organic layers were washed once with 200 ml water, dried (Na2SO4) and evaporated to afford 25.59 g (136 mmol, 95% yield) of the title compound as a yellow solid, which was used in the next steps without further purification. LCMS: (M+H)=189; tR=0.64 min (LC-MS 1). 1H-NMR (d6-DMSO, 400.43 MHz) δ ppm 9.23 (s, 1H) 8.45 (s, 1H) 3.61 (s, 3H).

1. additionwas added at 0° C.
2. concentrationThe reaction mixture was concentrated
3. additiondiluted with 300 ml water
4. extractionextracted twice with 400 ml EtOAc
5. washThe combined organic layers were washed once with 200 ml water
6. dry with materialdried (Na2SO4)
7. customevaporated

ORD record

ord-f0346fef413d423aa13057baa62a565d

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403827B2