反应详情

温度

20 °C

33.8 g (55 mmol) of oxone [70693-62-8] are added in portions to a solution of 13.5 g (100 mmol) of 2-nitro-4-methylbenzaldehyde [20357-22-6] and 11.9 g (110 mmol) of 1,2-diaminobenzene in a mixture of 150 ml of DMF and 5 ml of water with stirring and cooling to 20° C. at such a rate that the temperature does not exceed 35° C. The reaction mixture is subsequently stirred at room temperature until conversion of the aldehyde is complete (about 4 h). The reaction mixture is stirred into a solution of 40 g of potassium carbonate in 2000 ml of water, stirred for a further 15 min., extracted with three 300 ml portions of dichloromethane in each case, the organic phase is washed twice with 300 ml of water, once with 500 ml of sat. sodium chloride solution and dried over sodium sulfate. The dichloromethane solution is filtered through silica gel, and the dichloromethane is removed in vacuo. The yellow residue is taken up in 500 ml of methanol, blanketed with nitrogen with stirring, 3 g of 10% Pd/C are added, and the mixture is hydrogenated at room temperature in an autoclave at a hydrogen pressure of 2 bar. When the uptake of hydrogen is complete, the catalyst is filtered off via a Celite bed, and the methanol is removed in vacuo. Yield: 18.5 g (83 mmol), 83%. Purity: >95% according to 1H-NMR.

1. customdoes not exceed 35° C
2. custom(about 4 h)
3. stirringstirred for a further 15 min.
4. extractionextracted with three 300 ml portions of dichloromethane in each case
5. washthe organic phase is washed twice with 300 ml of water, once with 500 ml of sat. sodium chloride solution
6. dry with materialdried over sodium sulfate
7. filtrationThe dichloromethane solution is filtered through silica gel
8. customthe dichloromethane is removed in vacuo
9. stirringwith stirring
10. addition3 g of 10% Pd/C are added
11. customis hydrogenated at room temperature in an autoclave at a hydrogen pressure of 2 bar
12. filtrationthe catalyst is filtered off via a Celite bed
13. customthe methanol is removed in vacuo