2-Benzyl-4-nitroisoindoline → Isoindolin-4-amine

HRID 1494826Notes

Reaction equation

HRID 1494826 reaction equation
C([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:17]([O-])=O)[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[NH2:17][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH2:16][NH:8][CH2:9]2

Participants

4

Reactant 1

HCID 147958602-Benzyl-4-nitroisoindoline

Product 1

HCID 14795861Isoindolin-4-amineYield 61.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

11.5 g of 2-benzyl-4-nitroisoindoline was dissolved in 150 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 one day at room temperature and for another 5 days at 40° C.. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by a vacuum distillation (bath temperature: 150°-180° C., pressure: 0.1 mmHg) to obtain 3.74 g of 4-aminoisoindoline.

Workup

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

Sources & evidence

ORD record
ord-044d71713e844378a4a53ff6ebfbc9cd
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

Loading…