Isatoic Anhydride → 2-Amino-N-methoxybenzamide

Participants

Reaction Steps

O-methylhydroxylamine hydrochloride (1.79 g) was added to isatoic anhydride (2.34 g) in THF (72 mL) and DIPEA (4 mL). The reaction was stirred for 3 hours and then heated to reflux overnight. The reaction was then cooled and concentrated in vacuo and the residue dissolved in EtOAc (100 mL) and saturated aqueous sodium bicarbonate solution (100 mL). The phases were separated and the organics were washed with saturated aqueous sodium bicarbonate solution (2×100 mL). The organics were extracted with 1 M HCl (4×25 mL), the aqueous phase basified with potassium carbonate (˜15 g) and the organics discarded. The aqueous was then extracted with EtOAc (3×75 mL). The combined organics were dried (MgSO4, 20 g) and concentrated. The product was dried overnight at 40° C. under vacuum to give 2-amino-N-methoxybenzamide (1.18 g, 50% yield).

Provenance & Evidence