Реакция #487552

Уравнение реакции

Ammonium nitrate

4-ethylaniline

→

4-ethyl-3-nitroaniline

Выход 75.2%

Растворители

sulfuric acid

Условия реакции

Обработка

1. 1
   Температураmaintaining the temperature at −10° C. to 0° C. by external cooling
2. 2
   workup.ADDITIONpoured
3. 3
   Другоеonto crushed ice
4. 4
   Фильтрацияthe precipitate is collected by filtration
5. 5
   workup.ADDITIONthe solution made neutral by addition of dilute aqueous sodium hydroxide solution
6. 6
   Экстракцияextracted with ethyl acetate
7. 7
   Сушкаdried over anhydrous sodium sulfate
8. 8
   Фильтрацияfiltered
9. 9
   Другоеthe filtrate is evaporated in vacuo

Методика

Ammonium nitrate (39.6 g, 0.49 mol) is added portionwise to a chilled (ice-bath) solution of 4-ethylaniline (20 g, 0.16 mol) in concentrated sulfuric acid (100 ml), maintaining the temperature at −10° C. to 0° C. by external cooling. The reaction mixture is stirred for two hours, then poured onto crushed ice, and the precipitate is collected by filtration. The solid is taken up in water, the solution made neutral by addition of dilute aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous sodium sulfate, filtered and the filtrate is evaporated in vacuo to give 4-ethyl-3-nitroaniline (20 g).

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