反应详情

温度

110 °C

A 3-neck round bottom flask was equipped with a condenser. The flask was loaded with 4-chloro-3,5-dinitrobenzonitrile (4.5 g, 19.18 mmol) and acetic acid (60 mL). The solution was heated to 110° C. Iron (powder) (2.5 g, 44.8 mmol) was added slowly (in three portions), saw bubbling and also color changed to dark red. The mixture was stirred vigorously for 2 h at 110° C. LC-MS indicated desired monoamine and diamine. Then it was cooled to room temperature and diluted with DCM and saturated aqueous sodium bicarbonate solution was slowly added to neutralize. After separating the layers, the aqueous layer was further extracted with DCM. The combined organic extracts were washed with water, brine, dried over MgSO4, filtered and concentrated. Purification via flash chromatography (0-20% EtOAc in DCM, 120 g) gave 3-amino-4-chloro-5-nitrobenzonitrile (1.8 g) and 3,5-diamino-4-chlorobenzonitrile (1 g) as bright yellow solid and brown solid respectively.

1. customA 3-neck round bottom flask was equipped with a condenser
2. customsaw bubbling
3. temperatureThen it was cooled to room temperature
4. additiondiluted with DCM and saturated aqueous sodium bicarbonate solution
5. additionwas slowly added
6. customAfter separating the layers
7. extractionthe aqueous layer was further extracted with DCM
8. washThe combined organic extracts were washed with water, brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated
12. customPurification via flash chromatography (0-20% EtOAc in DCM, 120 g)