Methyl iodide → 5-Chloro-1-methyl-3-nitropyridin-2-one

Temperatur

0 °C

A solution of 5-chloro-2-hydroxy-3-nitropyridine (15.0 g, 86 mmol) in DMF (200 ml) was cooled down to 0° C. under argon. Then NaH (4.13 g, 103 mmol) was added by portions in 25 min and the reaction mixture was stirred at 0° C. for 1 hour. After that CH3I (8.06 ml, 129 mmol) was added dropwise and the ice-bath was removed. The reaction mixture was stirred at RT for 4 hours. The solution was concentrated and then the slurry mixture was taken in 250 ml water and extracted twice with 300 ml ethyl acetate. The combined organic phases were washed twice with 200 ml brine, dried (Na2SO4) and evaporated to dryness to afford 14.63 g (78 mmol, 90% yield) of the title compound as dark yellow solid. LCMS: (M+H)=189; tR=0.55 min (LC-MS 4). HPLC: tR=1.77 min (HPLC 5). 1H-NMR (d6-DMSO, 400 MHz) δ ppm 8.53 (s, 2H) 3.52 (s, 3H).

1. customthe ice-bath was removed
2. stirringThe reaction mixture was stirred at RT for 4 hours
3. concentrationThe solution was concentrated
4. extractionextracted twice with 300 ml ethyl acetate
5. washThe combined organic phases were washed twice with 200 ml brine
6. dry with materialdried (Na2SO4)
7. customevaporated to dryness

ORD-Eintrag

ord-747705f6ee674015b0c49e82c5190a27

Quelldatensatz

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09403827B2