Isatoic Anhydride → 2-Amino-N-methoxybenzamide

To a mixture of isatoic anhydride (40 g, 245.39 mmol, 1 eq) and o-methyl hyroxylamine hydrochloride (30.55 g, 368.09 mmole, 1.5 eq) in EtOH:H2O (9:1) (1000 mL) was added triethylamine (51.2 mL, 368.09 mmole, 1.5 eq) and resulting mixture was reflux for 4 h. After completion of reaction solvent was removed under reduced pressure and residue was diluted with water (500 mL), extracted with ethyl acetate (3×250 mL). Combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Solid compound so obtained was purified by washing with diethyl ether and hexane to give the title compound as brown solid (20 g, 49%). 1H-NMR (400 MHz, DMSO-d6): δ 3.67 (s, 3H), 6.20-6.40 (brs, 2H), 6.44-6.53 (m, 1H), 6.70 (d, 1H, J=7.76 Hz), 7.10-7.19 (m, 1H), 7.30 (d, 1H, J=7.6 Hz), 11.40 (s, 1H). LC-MS [M+H]+=167.2.

1. customresulting mixture
2. temperaturewas reflux for 4 h
3. customAfter completion of reaction solvent
4. customwas removed under reduced pressure and residue
5. additionwas diluted with water (500 mL)
6. extractionextracted with ethyl acetate (3×250 mL)
7. dry with materialCombined organic layer was dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customSolid compound so obtained
11. customwas purified
12. washby washing with diethyl ether and hexane

ORD record

ord-52a3a2351bd64419a647a95f6ff79490

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09446034B2