反应详情

温度

80 °C

To a solution of ethyl 2-ethoxy-4-nitro-benzoate (12.7 g, 53.1 mmol) in ethanol (94 mL) was added a solution of ammonium chloride (56 mL). The formation of a precipitate was observed. Iron (15.2 g, 271 mmol) was added and the reaction mixture was heated at 80° C. for 16 h. The reaction mixture was cooled and filtered through Celite, and the Celite was rinsed with methylene chloride. Water was added and the product was extracted three times with methylene chloride. The organic layers were dried over magnesium sulfate and concentrated. Purification of the crude residue by flash column chromatography (silica gel, eluting with 0-3% methanol in chloroform) gave ethyl 4-amino-2-ethoxy-benzoate as a tan solid (10.3 g, 99%).

1. temperatureThe reaction mixture was cooled
2. filtrationfiltered through Celite
3. washthe Celite was rinsed with methylene chloride
4. additionWater was added
5. extractionthe product was extracted three times with methylene chloride
6. dry with materialThe organic layers were dried over magnesium sulfate
7. concentrationconcentrated
8. customPurification of the crude residue
9. washby flash column chromatography (silica gel, eluting with 0-3% methanol in chloroform)