Isatoic Anhydride → 2-Amino-N-methoxybenzamide

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).

1. temperatureheated
2. temperatureto reflux overnight
3. temperatureThe reaction was then cooled
4. concentrationconcentrated in vacuo
5. dissolutionthe residue dissolved in EtOAc (100 mL)
6. customThe phases were separated
7. washthe organics were washed with saturated aqueous sodium bicarbonate solution (2×100 mL)
8. extractionThe organics were extracted with 1 M HCl (4×25 mL)
9. extractionThe aqueous was then extracted with EtOAc (3×75 mL)
10. dry with materialThe combined organics were dried (MgSO4, 20 g)
11. concentrationconcentrated
12. customThe product was dried overnight at 40° C. under vacuum

ORD record

ord-fe55ab4f1054415da4c57a1e1fb0212f

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569298B2