Triethylamine → N-methoxy-N,3-dimethyl-4-nitrobenzamide

Participants

Reaction Steps

Triethylamine (37.9 mL, 273 mmol) was added slowly to a mixture of 3-methyl-4-nitrobenzoic acid (25.0 g, 136 mmol), N,O-dimethylhydroxylamine hydrochloride (14.95 g, 150.3 mmol), and EDCI (31.40 g, 163.9 mmol) in DCM (171 mL). The mixture was stirred at room temperature overnight, quenched with saturated aqueous NaHCO3 and stirred at room temperature for 30 minutes. Water (50 mL) was added followed by additional DCM. The mixture was stirred for 10 minutes and layers were separated. The aqueous layer was again extracted with DCM. The combined organic layers were dried over MgSO4, then filtered. The solvent was removed and the residual oil chromatographed (0 to 20% EtOAc/DCM) to provide the title compound as a yellow oil.

Provenance & Evidence