Reaction #487552

Reaction equation

Ammonium nitrate

4-ethylaniline

→

4-ethyl-3-nitroaniline

Yield 75.2%

Solvents

sulfuric acid

Conditions

Workup

1. 1
   Temperaturemaintaining the temperature at −10° C. to 0° C. by external cooling
2. 2
   workup.ADDITIONpoured
3. 3
   Otheronto crushed ice
4. 4
   Filtrationthe precipitate is collected by filtration
5. 5
   workup.ADDITIONthe solution made neutral by addition of dilute aqueous sodium hydroxide solution
6. 6
   Extractionextracted with ethyl acetate
7. 7
   Dryingdried over anhydrous sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Otherthe filtrate is evaporated in vacuo

Procedure

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).

Source