反应详情

To a solution of benzyl-(2-nitro-phenyl)-amine (1068) (2.5 g, 10.43 mmol) in ethanol (150 mL) and water (10 mL) was added iron (8.7 g, 155.7 mmol) followed by 30 drops of concentrated HCl, and the resulting mixture was heated overnight at reflux. The reaction mixture was quenched with water, diluted with DCM and the layers were separated. The organic layer was washed with saturated sodium bicarbonate solution, brine, dried over sodium sulfate and concentrated to give a brown oily residue. Further purification by column chromatography (SiO2, 20% ethyl acetate/hexanes) afforded N-benzyl-benzene-1,2-diamine (1069) as a dark yellow oil (1.18 g, 57%). 1H NMR (400 MHz, CDCl3) 7.41-7.24 (m, 5H), 6.82-6.67 (m, 4H), 4.32 (s, 2H), 3.56 (b, 3H, NH).

1. temperaturethe resulting mixture was heated overnight
2. temperatureat reflux
3. customThe reaction mixture was quenched with water
4. additiondiluted with DCM
5. customthe layers were separated
6. washThe organic layer was washed with saturated sodium bicarbonate solution, brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. customto give a brown oily residue
10. customFurther purification by column chromatography (SiO2, 20% ethyl acetate/hexanes)