Methyl iodide → N-(2-Methoxy-5-nitro-phenyl)-N-methyl-propionamide

Temperature

0 °C

To a stirred solution of 11.2 g (50.0 mmol) of (2) in 150 mL of anhydrous THF at 0° C. under the nitrogen, was added 3.0 g (75 mmol) of NaH (60% in oil). The suspension was stirred for 0.5 h at 0° C. and 10 mL (150 mmol) of iodomethane was added at 0° C. After the mixture warmed to room temperature and stirred for 3 h, the reaction was quenched by ice brine and extracted with EtOAc (200 mL). The organic phase was washed with brine, dried (Na2SO4), filtered, evaporated in vacuo and the solid was washed with hexane/EtOAc (9:1) to give pure product N-(2-Methoxy-5-nitro-phenyl)-N-methyl-propionamide (3) as a light yellow solid (11.3 g, 95% yield).

1. temperatureAfter the mixture warmed to room temperature
2. stirringstirred for 3 h
3. customthe reaction was quenched by ice brine
4. extractionextracted with EtOAc (200 mL)
5. washThe organic phase was washed with brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. customevaporated in vacuo
9. washthe solid was washed with hexane/EtOAc (9:1)

ORD record

ord-62428e6c89a84a82b95b84e8167a23b5

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08034834B2