反应详情

温度

5 °C

A solution of 3-methoxyaniline (2.21 g) in acetic acid (3 ml) and acetic anhydride (10 ml) was stirred at room temperature for 1 hour. The solution was cooled to 5° C. and 60% nitric acid (1 ml) was added dropwise with stirring. When the cooling bath was removed, whereupon the solution temperature rose to 60° C. The solution was allowed to cool down to room temperature, poured into ice-water (100 ml) and neutralized with sodium hydroxide. The separated crystals were collected by suction and washed with water. To the crystals was added 4N hydrochloric acid (45 ml) and the mixture was refluxed for 2 hours. The reaction mixture was alkalized with sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent: chloroform) to give 0.67 g of 5-methoxy-2-nitroaniline.

1. customWhen the cooling bath was removed, whereupon the solution temperature
2. customrose to 60° C
3. temperatureto cool down to room temperature
4. additionpoured into ice-water (100 ml)
5. customThe separated crystals were collected by suction
6. washwashed with water
7. additionTo the crystals was added 4N hydrochloric acid (45 ml)
8. temperaturethe mixture was refluxed for 2 hours
9. extractionextracted with ethyl acetate
10. washThe organic layer was washed with saturated aqueous sodium chloride solution
11. dry with materialdried over anhydrous magnesium sulfate
12. distillationThe solvent was distilled off under reduced pressure
13. customthe residue was purified by silica gel chromatography (eluent: chloroform)