Acetic Acid → 6-Nitro-1,3-benzodioxol-5-amine

Participants

Reaction Steps

NaOMe (4.82 g, 89.2 mmol) was added to a stirred solution of nitroacetamide 219 (5.0 g, 22.3 mmol) in MeOH (100 mL) at reflux temperature and the mixture stirred at reflux temperature for 15 min. HOAc (25 mL, 446 mmol) was added to quench the reaction and the solvent evaporated. Toluene (2×50 mL) was added and the azeotrope evaporated. The residue was dissolved in DCM (100 mL) and filtered through a short column of silica to give nitroaniline 220 (3.25 g, 80%) as an orange solid: mp 199-201° C. [lit (Krasso, A. & Ramuz, H., U.S. Pat. No. 4,599,347, 1986) mp (iPrOH) 203-204° C.]; 1H NMR δ 7.53 (s, 1H, H-7), 6.30 (br s, 2H, NH2), 6.22 (s, 1H, H-4), 5.98 (s, 2H, H-2).

Provenance & Evidence