1,3-Benzodioxole-5-carboxylic acid → N-methoxy-N-methylbenzo[d][1,3]dioxole-5-carboxamide

Participants

Reaction Steps

To a solution of benzo[1,3]dioxole-5-carboxylic acid (69 g, 415 mmol) in dimethylformamide (1L) was added di-imidazol-1-yl-methanone (74 g, 1.1 equiv), and the resulting reaction mixture was stirred at ambient temperature for 90 minutes. N,O-Dimethyl-hydroxylamine (43 g, 1.1 equiv) was added to the reaction mixture. The resulting reaction mixture was stirred at ambient temperature for 18 hours, and then concentrated in vacuo to ¼ of the volume, poured into 5% aqueous sodium hydrogen carbonate (1L), stirred at ambient temperature for 20 minutes, and then extracted with methyl tert-butyl ether (2×300 mL). The combined organics extracts were dried over magnesium sulfate and concentrated in vacuo. The resulting residue was azeotroped with toluene (800 mL) and dried under vacuum for 3 hours. The crude product was used in the next step without further purification.

Provenance & Evidence