2-Chloro-3-methyl-5-nitropyridine → 6-Chloro-5-methylpyridin-3-amine
反応式
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1>O.CC(O)=O.[Fe]>[NH2:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Cl:1])=[N:3][CH:4]=1参加物
4
実験手順
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)+.
後処理
- temperaturewhile maintaining the temperature below 40° C.
- filtrationThe mixture was filtered through celite
- extractionthe aqueous filtrate was extracted with EtOAc (4×)
- washThe filter cake was washed with EtOAc
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customchromatographed (silica gel; CHCl3 /MeOH, 98:2)
出典と根拠
- ORDレコード
- ord-fb181b43b2cf48a49bb845d00e4222a4
- 出典データセット
- uspto-grants-1998_03
- 特許番号
- US05733912
反応ノート
読み込み中…