反应详情

To a suspension of sodium hydride (60%, 2.70 g (67.5 mmol)) in THF (100.0 ml), under cooling with ice and with stirring, 4-amino-3-nitrophenol (10.0 g (64.9 mmol)) was added. To the resulting mixture, after 10 minutes' stirring under cooling with ice, chloromethyl methyl ether (5.50 g (68.3 mmol)) was added dropwise and the mixture was stirred at 5° C. for one hour and at room temperature for one hour, and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and saturated aqueous solution of sodium bicarbonate successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. Then the residue was subjected to silica gel column chromatography with chloroform-ethanol (100:1) as eluent to give 7.69 g (60%) of 4-methoxymethoxy-2-nitroaniline as red oil.

1. temperatureunder cooling with ice
2. stirringTo the resulting mixture, after 10 minutes' stirring
3. additionwas added dropwise
4. stirringthe mixture was stirred at 5° C. for one hour and at room temperature for one hour
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in ethyl acetate
7. washwashed with water and saturated aqueous solution of sodium bicarbonate successively
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure