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

HRID 2420193Notes

Reaction equation

HRID 2420193 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-ee2ca71ffec3468e9f5b96242ab9d017
Source dataset
uspto-grants-1978_08
Patent number
US04110103

Reaction notes

Loading…