Maleic Anhydride → 1-[4-(Methylphenylamino)butyl]-1H-pyrrole-2,5-dione

HRID 1733865Notes

Reaction equation

HRID 1733865 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH3:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:14]1(=O)[O:19][C:17](=[O:18])[CH:16]=[CH:15]1>ClCCl>[C:14]1(=[O:19])[N:1]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH3:13])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:17](=[O:18])[CH:16]=[CH:15]1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 19438630N1-Methyl-N1-phenylbutane-1,4-diamine

Product 1

HCID 194386241-[4-(Methylphenylamino)butyl]-1H-pyrrole-2,5-dioneYield 19.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-Aminobutyl)-N-methylaniline (7.2 g) was dissolved in dichloromethane (70 ml) and maleic anhydride (4 g) was added thereto. The mixture was stirred at room temperature for 2 hours. The solvent was distilled off and then acetic anhydride (10 ml) was added. The resulting mixture was stirred at 100° C. for 5 hours. After concentration, an aqueous sodium bicarbonate was added to the residue to neutralize it. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with hexane/ethyl acetate (2:1) to obtain the desired compound (2.0 g) as yellow needles.

Workup

  1. distillationThe solvent was distilled off
  2. additionacetic anhydride (10 ml) was added
  3. stirringThe resulting mixture was stirred at 100° C. for 5 hours
  4. concentrationAfter concentration
  5. additionan aqueous sodium bicarbonate was added to the residue
  6. extractionThe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. washeluted with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-0c7c4d30e2c14fc6bfeefb47e86ac243
Source dataset
uspto-grants-1996_07
Patent number
US05532171

Reaction notes

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