2-Benzyl-5-nitroisoindoline → 2,3-Dihydro-1H-isoindol-5-amine

HRID 1494827Notes

Reaction equation

HRID 1494827 reaction equation
C([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:17]([O-])=O)[CH:14]=2)[CH2:9]1)C1C=CC=CC=1>[Pd].CO>[NH2:17][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:16]2

Participants

4

Reactant 1

HCID 120659772-Benzyl-5-nitroisoindoline

Product 1

HCID 147958622,3-Dihydro-1H-isoindol-5-amineYield 77.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7.23 g of 2-benzyl-5-nitroisoindoline was dissolved into 100 ml of methanol and to the solution was added 1.5 g of 10% palladium on carbon. The mixture was stirred under a hydrogen gas stream under atmospheric pressure for 2 days at room temperature and another 5 days at 40° C. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by vacuum distillation (bath temperature: 150°-180° C., pressure: 0.1 mmHg) to obtain 2.94 g of 5-aminoisoindoline.

Workup

  1. customanother 5 days
  2. customat 40° C
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. distillationThe residue was purified by vacuum distillation (bath temperature: 150°-180° C., pressure: 0.1 mmHg)

Sources & evidence

ORD record
ord-e41be8e633cb4b0ea8690d7ee47d885e
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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