Water → 1,4-Dimethylpyridin-2(1H)-one

To a suspension of 4-methy-2(1H)-pyridone (5 g, 45.82 mmol) and potassium carbonate (12.64 g, 91.64 mmol) in DME (100 mL) was added iodomethane (50.5 g, 366 mmol) at room temperature and the reaction mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature, poured into water (200 mL) and was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with brine solution (200 mL) and were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration gave the crude product which was purified by silica gel chromatography on a Biotage (40m) column to afford 2.5 g (44% yield) of 1,4-dimethyl-2(1H)-pyridone as an amorphous white solid. FAB-HRMS m/e calcd for C7H9NO (M+H) 123.0241, found 123.0246

1. temperaturethe reaction mixture was heated
2. temperatureto reflux overnight
3. extractionwas extracted with ethyl acetate (3×100 mL)
4. washThe combined extracts were washed with brine solution (200 mL)
5. dry with materialwere dried over anhydrous magnesium sulfate
6. filtrationFiltration of the drying agent and concentration
7. customgave the crude product which
8. customwas purified by silica gel chromatography on a Biotage (40m) column

ORD record

ord-c5a1a0184b0b459ca757385152ceafeb

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06388084B1