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

HRID 1902173

Reaction equation

HRID 1902173 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-31bdf4ae6a4a4b9580e03cd430ceb9c7
Source dataset
uspto-grants-1982_12
Patent number
US04362548

Linked notes

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