Ethyl Acetate → 4-(3-Aminophenyl)-6-bromo-5,7-dimethyl-2H-chromen-2-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-bromo-5,7-dimethyl-4-(3-nitrophenyl)-2H-chromen-2-one (6-3) (15.41 g, 41.18 mmol) in EtOH (100 mL) and acetic acid (40 mL) was added iron (11.50 g, 205.9 mmol) at room temperature. The mixture was heated at 110° C. for 2 h. The reaction mixture was cooled at room temperature and filtrated. To the filtrate was added EtOAc and Na2CO3 (37 g, 0.35 mol) in water (200 mL). After being stirred at room temperature, the mixture was filtrated. Then the filtrated was diluted with EtOAc and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4, and concentrated. To the concentrate added CH2Cl2-MeOH (1:9), and the precipitated solid was collected by filtration. The solid was washed with CH2Cl2-MeOH (1:9) and purified by silica gel column chromatography (hexanes:EtOAc=2:1˜1:1) to give the title compound 6-4 (2.44 g, 17% yield) as a yellow solid.

Provenance & Evidence