Acetic Acid → 2-(1H-pyrrol-1-yl)aniline

HRID 429651Notes

Reaction equation

HRID 429651 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N+:12]([O-])=O)[CH:5]=[CH:4][CH:3]=[CH:2]1.C(O)(=O)C>C(O)C.[Fe]>[N:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH2:12])[CH:2]=[CH:3][CH:4]=[CH:5]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 5206111-(2-Nitrophenyl)pyrrole

Product 1

HCID 801232-(1H-pyrrol-1-yl)anilineYield 92.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(1-pyrrolyl)nitrobenzene (1.11 g) in ethanol (30 ml) were added iron powder (1.65 g) and acetic acid (3.54 g) and the mixture was refluxed for 1 hour. The reaction mixture was filtered through a bed of celite and the filtrate was concentrated in vacuo. The residue was diluted with a mixture of ethyl acetate and saturated aqueous sodium bicarbonate solution and the mixture was filtered through a bed of celite again. The organic layer was separated and washed with water and brine. The solution was dried over sodium sulfate and the solvent was evaporated in vacuo to give 2-(1-pyrrolyl)phenylamine (860 mg).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. filtrationThe reaction mixture was filtered through a bed of celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was diluted with a mixture of ethyl acetate and saturated aqueous sodium bicarbonate solution
  5. filtrationthe mixture was filtered through a bed of celite again
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialThe solution was dried over sodium sulfate
  9. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-1df4deed1d2e4fc6ae64460029a1deab
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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