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-4e379a2101e1400886bcbe72c6742a30

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108933B2