Ethyl Acetate → Methyl 2-(methyl(4-nitrobenzyl)amino)acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(bromomethyl)-4-nitrobenzene (1 g, 4.63 mmol), methyl 2-(methylamino)acetate hydrochloride (0.646 g, 4.63 mmol), and K2CO3 (0.960 g, 6.94 mmol) in CH3CN (20 ml) was heated under MW irradiation at 60° C. for 1.5 hours. The mixture was portioned between EtOAc and water, and the organic layer was washed with brine ad dried over Na2SO4. The solvent was removed and the crude was purified by filtration on SCX cartridge (DCM/MeOH 1/1; MeOH/conc.aq.NH4OH 90/10). The basic fraction was evaporated to dryness to give methyl 2-(methyl(4-nitrobenzyl)amino)acetate (0.800 g, 3.36 mmol, 72.5% yield, MS/ESI+ 239.1 [MH]+).

Provenance & Evidence