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 (40 m) 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. b) Preparation of 1,4-dimethyl-3-iodo-2(1H)-pyridone and 1,4-dimethyl-5-iodo-2(1H)-pyridone

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 (40 m) column

ORD record

ord-6c791bc031f34e8eacef3f7f9e144bd8

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06916933B2