2-Morpholin-4-yl-8-(1-nitro-dibenzofuran-4-yl)-1-benzopyran-4-one → 8-(1-Amino-dibenzofuran-4-yl)-2-morpholin-4-yl-1-benzopyran-4-one

Participants

Reaction Steps

To a solution of 2-morpholin-4-yl-8-(1-nitro-dibenzofuran-4-yl)-1-benzopyran-4-one (32, 2.5 mmol, 1.11 g) in acetic acid (50 ml) was added zinc dust (25 mmol, 1.64 g), portionwise over ten minutes. The mixture was then stirred at room temperature for 2 hrs, whereupon it was filtered through a Celite™ pad which was washed with methanol (20 ml) and CH2Cl2 (20 ml). Solvents were removed in vacuo to give a slurry which was then diluted with ammonia hydroxide (30 ml) and the resulting solid removed by filtration. The residue was purified by flash chromatography (SiO2) using MeOH; CH2Cl2-1:99 as eluent to give the desired product (75%) in analytically pure form. m/z 413.5 [M+H]+ (Rt=4.27 min).

Provenance & Evidence