反应详情

p-Nitroaniline (0.51 g, 3.7 mmol) was added to a solution of 4,6-dimethyl-pyridine-2-carbaldehyde (0.5 g, 3.7 mmol) in tetrahydrofuran (20 mL) at 0° C., followed by sulfuric acid and water (1 mL:1 mL). After stirring at 0° C. for 30 min. sodium cyanoborohydride (0.47 g, 7.4 mmol) was added portionwise at 0° C. The mixture stirred at room temperature for 1 h then concentrated in vacuo, diluted with water and extracted with ethyl acetate. The organic phase was washed with sodium carbonate solution, dried over anhydrous sodium sulfate and concentrated to give a residue which was purified by column chromatography on silica gel (60-120 mesh) using 18% ethyl acetate/hexane as eluent to afford (4,6-dimethyl-pyridin-2-ylmethyl)-(4-nitro-phenyl)-amine (0.35 g, 37%).

1. additionwas added portionwise at 0° C
2. concentrationthen concentrated in vacuo
3. additiondiluted with water
4. extractionextracted with ethyl acetate
5. washThe organic phase was washed with sodium carbonate solution
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated
8. customto give a residue which
9. customwas purified by column chromatography on silica gel (60-120 mesh)