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

HRID 22392

Reaction equation

HRID 22392 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].[CH2:13]([CH2:17][C:18](=O)[CH3:19])[C:14]([CH3:16])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C>C1(C)C=CC=CC=1>[CH3:19][C:18]1[N:1]([N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[C:14]([CH3:16])=[CH:13][CH:17]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 6101p-Toluenesulfonic acidHCID 80352,5-HexanedioneHCID 74645N-Aminophthalimide

Product 1

HCID 28171692-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred suspension of N-aminophthalimide (19.75 g), acetonylacetone (14.3 ml), p-toluenesulfonic acid (5 mg), and toluene (406 ml) was heated at reflux for 1 hour and cooled to room temperature. The reaction mixture was combined with another reaction mixture and the entire mixture decolorized with activated charcoal. Filtration through a bed of celite gave a solution which upon partial concentration resulted in crystallization of the desired product as a solid (11.0 g), m.p. 182.5°-183.5° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. filtrationFiltration through a bed of celite
  4. customgave a solution which
  5. concentrationupon partial concentration

Sources & evidence

ORD record
ord-a69fea757be74b9d8c7eb8ead0a2cf84
Source dataset
uspto-grants-1995_06
Patent number
US05428053

Linked notes

Loading…