Sulfuric Acid → 2-Ethyl-6-nitroaniline

HRID 2203213Notes

Reaction equation

HRID 2203213 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[NH:12]C(=O)C)[CH3:2].OS(O)(=O)=O>O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[NH2:12])[CH3:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 14147006N-(2-ethyl-6-nitrophenyl)acetamide

Product 1

HCID 224824552-Ethyl-6-nitroanilineYield 25.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of crude N-(2-ethyl-6-nitrophenyl)acetamide (2.4 g, 12 mmol), H2SO4 (3.4 g, 36 mmol), and H2O (10 mL) was refluxed for 2 hours and steam distilled. The distillate was extracted with Et2O and the organic phase was washed with brine and dried over Na2SO4. The solvent was evaporated to give the title compound as a yellow liquid (0.5 g, 25%). 1H NMR (400 MHz, CD3OD) δ 7.95 (1H, d, J=8.8 Hz), 7.31 (1H, d, J=6.8 Hz), 6.62 (1H, dd, J=8.8, 7.6 Hz), 2.63 (2H, q, J=7.6 Hz), 1.27 (3H, t, J=7.6 Hz).

Workup

  1. temperaturewas refluxed for 2 hours
  2. distillationsteam distilled
  3. extractionThe distillate was extracted with Et2O
  4. washthe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2c2ed0de9b694dcba6d466a15b734451
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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