Isatoic Anhydride → 2-amino-N-(2-hydroxyethoxy)benzamide

Participants

Reaction Steps

1H-3,1-benzoxazine-2,4-dione (320 mg, 1.96 mmol) and 2-(aminooxy)ethanol hemisulfate (990 mg, 3.92 mmol) were reacting using the procedure of example 15.07, starting material. The crude product was purified by flash chromatography on silica gel eluting with 0 to 80% EtOAc in DCM. The solvent was evaporated to dryness to afford 2-amino-N-(2-hydroxyethoxy)benzamide (256 mg, 66.5%) as a pale yellow oil which solidified on standing. NMR Spectrum: (DMSOd6) 3.57-3.64 (m, 2H), 3.85-3.92 (m, 2H), 4.75 (bs, 1H), 6.27 (bs, 2H), 6.49 (dd, 1H), 6.71 (d, 1H), 7.15 (ddd, 1H), 7.34 (dd, 1H), 11.39 (bs, 1H); Mass spectrum: MH+ 197

Provenance & Evidence