4-Ethylaniline → 4-Ethyl-3-nitroaniline

HRID 1191534Notes

Reaction equation

HRID 1191534 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[NH4+].[CH2:6]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[CH3:7]>S(=O)(=O)(O)O>[CH2:6]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=1[N+:1]([O-:4])=[O:2])[CH3:7]

Participants

4

Reactant 2

HCID 115044-EthylanilineHCID 22985Ammonium nitrate

Product 1

HCID 227086804-Ethyl-3-nitroanilineYield 75.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

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° 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).

Workup

  1. temperaturemaintaining the temperature at −10° to 0° C. by external cooling
  2. additionpoured
  3. customonto crushed ice
  4. filtrationthe precipitate is collected by filtration
  5. additionthe solution made neutral by addition of dilute aqueous sodium hydroxide solution
  6. extractionextracted with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-fdf8dd690f2745a7826f31723a803bd8
Source dataset
uspto-grants-2014_03
Patent number
US08680012B2

Reaction notes

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