Acetic Acid → 3-Chloro-4-(1H-pyrrol-1-yl)aniline

HRID 2290546Notes

Reaction equation

HRID 2290546 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1.C(O)(=O)C>O.[Fe]>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)[NH2:8]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 4715112HCID 4715112, compound

Product 1

HCID 137686263-Chloro-4-(1H-pyrrol-1-yl)anilineYield 63%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A stirred mixture of 15.0 g (0.07 mole) of 1-(2-chloro-4-nitrophenyl)pyrrole and 30.0 g (0.53 mole) of iron powder in 100 ml of water was heated at reflux. During a three hour period 59.0 g (0.98 mole) of glacial acetic acid was added dropwise to the refluxing reaction mixture. Reflux was continued for one hour after complete addition. The mixture was cooled to room temperature, filtered and the filter cake rinsed with toluene. The filtrate was extracted with toluene (three 150 ml portions) and the extracts combined with the toluene rinse. The toluene solution was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to leave an oil which solidified. The solid was purified by column chromatography using silica gel and eluting with methylene chloride, to yield 8.5 g of 3-chloro-4-(pyrrol-1-yl)aniline.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperatureReflux
  4. additionafter complete addition
  5. filtrationfiltered
  6. washthe filter cake rinsed with toluene
  7. extractionThe filtrate was extracted with toluene (three 150 ml portions)
  8. washrinse
  9. dry with materialThe toluene solution was dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customThe filtrate was evaporated under reduced pressure
  12. customto leave an oil which
  13. customThe solid was purified by column chromatography
  14. washeluting with methylene chloride

Sources & evidence

ORD record
ord-5fe0b1bb6658432ab0bf43f967496b90
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

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