4-Ethylaniline → 4-Ethyl-3-nitroaniline

HRID 1430745Notes

Reaction equation

HRID 1430745 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-nitroaniline

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° 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 under reduced pressure to give 4-ethyl-3-nitroaniline.

Workup

  1. temperaturemaintaining the temperature at −10° C. 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 under reduced pressure

Sources & evidence

ORD record
ord-937229afd0024fc099450c57fb558763
Source dataset
uspto-grants-2015_01
Patent number
US08940913B2

Reaction notes

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