6-Nitrophthalide → 6-Aminophthalide

Participants

Reaction Steps

To a solution of 6-nitroisobenzofuran-1(3H)-one (15.0 g, 0.0800 mol) in HCl/H2O (375 mL/125 mL) was added SnCl2-2H2O (75.0 g, 0.330 mol). The reaction mixture was heated at reflux for 4 h, quenched with water, and extracted with ethyl acetate (300 mL×3). The organic layer was dried over Na2SO4 was evaporated in vacuo to give 6-aminoisobenzofuran-1(3H)-one (10.0 g, 78%). 1H NMR (300 MHz, CDCl3) δ 7.23 (d, J=8.1, 1H), 7.13 (d, J=2.1, 1H), 6.98 (dd, J=8.1, 2.1, 1H), 5.21 (s, 2H), 3.99 (br s, 2H).

Provenance & Evidence