铁粉还原硝基制备胺

硝基的还原是一种常用的合成伯胺的方法特别是芳香伯胺，一般而言，最干净和简便的还原方法就是通过Pd/C或Raney Ni加氢，但是当分子内存在对加氢敏感的官能团，如：卤素（Cl, Br and I; F 对加氢不敏感），双键，三键时，我们不得不采用其他方法， 最为经典的要数铁粉的还原。

反应实例

To the starting material (3.1 g) was added acetic acid (24.4 mL) and then, reduced iron powder (9.15 g), and the mixture was stirred for 16 hours at room temperature. The mixture was filtered with Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 1.4 g of the desired

product.

To 80 percent ethanol (5.0 mL), the starting material (300 mg, 1.76 mmol) and concentrated hydrochloric acid (0.45 ml, 5.28 mmol) were added to stir for 10 minutes at 20°C. Then, iron powder (500 mg, 8.95 mmol) was added to the mixture to further stirring for 1 hour at 20°C. Insoluble matters were filtered off and the filtrate was concentrated, adding 0.5N NaOH (10 mL) to the residue, filtering the solution to further remove insoluble matters, extracting the filtrate with chloroform, drying the extract over anhydrous sodium sulfate, concentrating the extract, and distilling the resulting crude product to afford 224 mg of the

desired compound (91% yield).

另外常用的条件还有，铁粉，氯化铵在甲醇和水混合溶液中回流。此类反应的后处理，一般情况下都是趁热过滤，防止冷却后，产品吸附到剩余的铁粉和氧化铁上。

另外由于铁粉反应后氧化物的颜色较深，不好纯化，有时会用锌粉代替铁粉进行反应，条件类似。