反应详情

2-Chloro-3-methyl-5-nitropyridine (15 g, 86.9 mmol; from Maybridge Chemical Co.) was dissolved in a solution of H2O/AcOH (5:1, 60 mL). Iron powder was added to the reaction mixture while maintaining the temperature below 40° C., and the mixture was stirred for 5 hours. The mixture was filtered through celite and the aqueous filtrate was extracted with EtOAc (4×). The filter cake was washed with EtOAc, and the EtOAc solutions were combined, dried (MgSO4), concentrated and chromatographed (silica gel; CHCl3 /MeOH, 98:2) to afford an orange solid (2.3 g, 89%): 1H NMR (CD3OD, 300 MHz) δ2.25 (s, 3H), 7.01 (d, J=2.0 Hz, 1H), 7.58 (d, J=2.0 Hz, 1H); MS (CI/NH3) m/z: 243/245 (M+H)+.

1. temperaturewhile maintaining the temperature below 40° C.
2. filtrationThe mixture was filtered through celite
3. extractionthe aqueous filtrate was extracted with EtOAc (4×)
4. washThe filter cake was washed with EtOAc
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customchromatographed (silica gel; CHCl3 /MeOH, 98:2)