2,5-Hexanedione → 2-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)-dione

HRID 893868

Reaction equation

HRID 893868 reaction equation
[NH2:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[CH3:13][C:14]([CH2:16][CH2:17][C:18]([CH3:20])=O)=O>C(O)(=O)C.C(Cl)Cl>[CH3:20][C:18]1[N:1]([N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])[C:14]([CH3:13])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 80352,5-HexanedioneHCID 74645N-Aminophthalimide

Product 1

HCID 28171692-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)-dioneYield 98%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-amino-phthalimide (50 g) and 2,5-hexadione (35.2 g) in 400 ml acetic acid was refluxed for 48 hours, stripped of solvent, slurried in methylene chloride and filtered. The filtrate was washed with saturated sodium bicarbonate solution, dried and stripped to yield N-(2,5-dimethylpyrrol-1-yl)-phthalimide (98%).

Workup

  1. temperaturewas refluxed for 48 hours
  2. filtrationfiltered
  3. washThe filtrate was washed with saturated sodium bicarbonate solution
  4. customdried

Sources & evidence

ORD record
ord-dfc76c2b2d994cfcb531a12813a8a835
Source dataset
uspto-grants-1981_08
Patent number
US04282028

Linked notes

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