Water → 1,9b-dihydro-3-isopropyl-3-methyl-5H-imidazo[2,1-a]isoindole2(3H),5-dione

HRID 441490Notes

Reaction equation

HRID 441490 reaction equation
[CH:1]([C:4]1([CH3:18])[N:8]2[C:9](=[O:16])[C:10]3[C:15]([C:7]2=[N:6][C:5]1=[O:17])=[CH:14][CH:13]=[CH:12][CH:11]=3)([CH3:3])[CH3:2].O.[H][H]>C(O)(=O)C>[CH:1]([C:4]1([CH3:18])[N:8]2[C:9](=[O:16])[C:10]3[C:15]([CH:7]2[NH:6][C:5]1=[O:17])=[CH:14][CH:13]=[CH:12][CH:11]=3)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 27292473-isopropyl-3-methyl-3H-imidazo[2,1-a]isoindole-2,5-dioneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 706213931,9b-dihydro-3-isopropyl-3-methyl-5H-imidazo[2,1-a]isoindole2(3H),5-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1.2 g 3-isopropyl-3-methyl-5H-imidazo[2,1-a]isoindole-2(3H), 5-dione in 75 ml acetic acid and 10 ml water containing 100 mg 5% palladium on carbon is shaken in an atmosphere of hydrogen at a pressure of 10 psi and room temperature. One equivalent of hydrogen is absorbed in 75 minutes. The mixture is filtered, and the filtrate concentrated under reduced pressure. To the residue is added toluene which is then removed in vacuo. This is repeated. To the gummy residue is added a small volume of acetonitrile to give the desired 1,9b-dihydro-3-isopropyl-3-methyl-5H-imidazo[2,1-a]isoindole-2(3H),5-dione as a crystalline solid identical to that prepared in Example 1.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. additionTo the residue is added toluene which
  4. customis then removed in vacuo
  5. additionTo the gummy residue is added a small volume of acetonitrile

Sources & evidence

ORD record
ord-58b1e16380944354a9456be2a22d2e73
Source dataset
uspto-grants-1977_08
Patent number
US04041045

Reaction notes

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