Methanol → N-(2H-1,3-Benzodioxol-5-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

Ac2O (21.4 mL, 226 mmol) was added dropwise to a stirred solution of 3,4-methylendioxyaniline (217) (25.87 g, 189 mmol) in dioxane (200 mL) at 0° C. and the mixture was stirred at 16° C. for 16 h. MeOH (10 mL) was added to decompose excess Ac2O and the solvent evaporated. The residue was dissolved in EtOAc (200 mL), dried and the solvent evaporated. The residue was filtered through a short column of silica, eluting with a gradient (50-100%) of EtOAc/pet. ether, to give acetamide 218 (29.17 g, 86%) as a white solid: mp 133-135° C. [lit (Krasso, A. & Ramuz, H., U.S. Pat. No. 4,599,347, 1986) mp (toluene) 138-139° C.]; 1H NMR δ 7.09 (d, J=1.8 Hz, 1H, H-4), 7.06 (br s, 1H, NH), 6.77 (dd, J=8.3, 1.8 Hz, 1H, H-6), 6.72 (d, J=8.3 Hz, 1H, H-7), 5.94 (s, 2H, H-2), 2.14 (s, 3H, CH3).

Provenance & Evidence