Isatoic Anhydride → 2-Amino-N-methoxybenzamide

A mixture of isatoic anhydride (5.0 g, 31 mmol) and methoxylamine hydrochloride (3.8 g, 46 mmol) in EtOH (100 mL) and H2O (10 mL) was charged with Triethylamine (6.4 mL, 46 mmol) and stirred at reflux for 4 h. The reaction mixture was concentrated in vacuo and partitioned between EtOAc and water and separated. The aqueous layer was extracted with EtOAc (3×) and the combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated. The obtained solid was washed with ether and hexanes to afford 4.5 g, 88% yield, of the title compound as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 11.40 (br. s., 1H), 7.30 (dd, J=1.14, 7.96 Hz, 1H), 7.09-7.19 (m, 1H), 6.70 (dd, J=0.76, 8.34 Hz, 1H), 6.45-6.52 (m, 1H), 6.30 (br. s., 2H), 3.67 (s, 3H); MS (ES+): m/z: 167.0783 [MH+]. HPLC: tR=0.83 min (UPLC TOF: polar—3 min).

1. temperatureat reflux for 4 h
2. concentrationThe reaction mixture was concentrated in vacuo
3. custompartitioned between EtOAc and water
4. customseparated
5. extractionThe aqueous layer was extracted with EtOAc (3×)
6. washthe combined organic fractions were washed with brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. washThe obtained solid was washed with ether and hexanes
11. customto afford 4.5 g, 88% yield

ORD record

ord-6fef4f7c370445ab88c8042688cd0656

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399433B2