反应详情

温度

110 °C

To a stirred solution of 4-nitrobenzene-1,2-diamine 2 (1.0 g, 6.53 mmol) in acetic acid (20 mL) was added ethyl 3-(3-bromophenyl)-3-oxopropanoate 1 (1.75 g, 6.53 mmol) at RT under inert atmosphere. The resulting reaction mixture was heated to 110° C. and stirred for 12 h. After complete consumption of the starting material (by TLC), the reaction mixture was cooled to RT and diluted with water (100 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure and the obtained crude was purified by silica gel column chromatography (eluent: 25% EtOAc/Hexane) to afford compound 3 (0.91 g, 39.5%) as yellow solid. 1H NMR (500 MHz, DMSO-d6): δ 10.91 (bs, 1H), 8.25 (s, 1H), 8.09-8.01 (m, 3H), 7.82 (d, J=6.4 Hz, 1H), 7.68 (d, J=7.6 Hz, 1H), 7.57-7.48 (m, 1H), 3.67 (s, 2H). MS (ESI): 361 [M+1]+

1. customThe resulting reaction mixture
2. customAfter complete consumption of the starting material (by TLC)
3. temperaturethe reaction mixture was cooled to RT
4. additiondiluted with water (100 mL)
5. extractionextracted with EtOAc (3×50 mL)
6. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
7. concentrationconcentrated under reduced pressure
8. customthe obtained crude
9. customwas purified by silica gel column chromatography (eluent: 25% EtOAc/Hexane)