Maleic Anhydride → 1-[3-(Pyridin-3-yloxy)propyl]-pyrrole-2,5-dione

HRID 272791Notes

Reaction equation

HRID 272791 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:2]=1.[C:12]1(=O)[O:17][C:15](=[O:16])[CH:14]=[CH:13]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[C:15](=[O:16])[CH:14]=[CH:13][C:12]2=[O:17])[CH:2]=1

Participants

5

Reactant 3

HCID 7923Maleic AnhydrideHCID 521998p-Toluenesulfonic acid monohydrateHCID 102195403-(3-Pyridyloxy)propylamine

Product 1

HCID 121099421-[3-(Pyridin-3-yloxy)propyl]-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

From 2 to 3 mmol of the appropriate 3-(pyridin-3-yloxy)propylamine in 5 ml of THF are admixed in succession with 500 mg of maleic anhydride (molecular mass: 98.06; 5.1 mmol) and 200 mg of p-toluenesulphonic acid hydrate (molecular mass: 190.22; 1.0 mmol). The solution is refluxed for 24 hours and concentrated to dryness. The residue is chromatographed on silica gel to give the desired 1-[3-(pyridin-3-yloxy)propyl]-pyrrole-2,5-dione derivative.

Workup

  1. temperatureThe solution is refluxed for 24 hours
  2. concentrationconcentrated to dryness
  3. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-47fb1ba4e7e04e60b4ee6c5475f7cd0c
Source dataset
uspto-grants-2008_11
Patent number
US07456202B2

Reaction notes

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