反应详情

温度

0 °C

Nitro compound 48 (97 mg, 2 mmol) was dissolved in a mixture of THF (7 mL) and MeOH (15 mL); NiCl2.×6H2O (130 mg, 0.5 mmol) was added and the solution was cooled to 0° C. To the cooled mixture NaBH4 (42 mg, 1.1 mmol) was added portion wise. The reaction was stirred for 20 min and quenched with 2 M HCl. The solvents were removed under reduced pressure and the residue was treated with concentrated ammonium hydroxide solution (pH 10) and extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate, filtered and evaporated. The residue was purified by column chromatography (eluent EtOAc) to afford the title compound 49 (46.7 mg, 51% yield) as a white solid. 1H NMR (DMSO) δ (ppm): 8.52 (d, J=5.5 Hz, 1H), 8.25 (s, 1H), 8.15 (d, J=8.4 Hz, 2H), 8.03 (d, J=8.4 Hz, 2H), 7.63-7.58 (m, 2H), 7.56-7.52 (m, 2H), 7.13 (t, J=8.6 Hz, 1H), 6.61 (d, J=2.2 Hz, 1H), 6.56 (dd, J=10 Hz, 1H), 6.46 (dd, J=5.7 Hz, 1H), 5.57 (s, 2H), 3.29 (s, 3H), MS (m/z): 414.8 (M+H).

1. addition×6H2O (130 mg, 0.5 mmol) was added
2. customquenched with 2 M HCl
3. customThe solvents were removed under reduced pressure
4. additionthe residue was treated with concentrated ammonium hydroxide solution (pH 10)
5. extractionextracted with EtOAc
6. extractionThe organic extract
7. dry with materialwas dried over anhydrous sodium sulfate
8. filtrationfiltered
9. customevaporated
10. customThe residue was purified by column chromatography (eluent EtOAc)