1,2-Dichloroethane → N-methoxy-N-methyl-2-(3-methylphenyl)acetamide

Participants

Reaction Steps

To a solution of (3-methylphenyl)acetic acid (1.0 g, 6.7 mmol) in DMF (20 mL0 were added N,O-dimethylhydroxylamine hydrochloride (0.78 g, 8.04 mmol), EDC (1.54 g, 8.04 mmol), HOBt (1.06. g, 8.04 mmol), and N,N-diisopropylethylamine (7.0 mL, 40.2 mmol). The solution was stirred at RT for 18 h then diluted with EtOAc (150 mL) and washed with HCl 1M (100 mL), water (100 mL), saturated solution of NaHCO3 (100 mL), and brine (100 mL). The organic solution was dried over sodium sulfate and concentrated in vacuo to afford the desired amide (1.2 g, 98%) used in the next step without further purification. Rf 0.8 (EtOAc/hexanes 1/1).

Provenance & Evidence