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

Temperature

0 °C

To a stirred solution of 11.2 g (500 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-c4b5c490692b4e868d568661cde3fb07

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09101614B2