4-Ethylaniline → 4-Ethyl-3-nitroaniline

HRID 43324

Reaction equation

HRID 43324 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 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 the extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo to give 4-ethyl-3-nitroaniline (20 g).

Workup

  1. temperaturemaintaining the temperature 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. extractionthe extracted with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-6814aaafeb0940e891be37b7237e7389
Source dataset
uspto-grants-2013_09
Patent number
US08536351B2

Linked notes

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