2-Benzyl-5-nitroisoindoline → 2-Benzyl-2,3-dihydro-1H-isoindol-5-ylamine

HRID 1494828Notes

Reaction equation

HRID 1494828 reaction equation
[CH2:1]([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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:17])[CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 120659772-Benzyl-5-nitroisoindoline

Product 1

HCID 31592442-Benzyl-2,3-dihydro-1H-isoindol-5-ylamineYield 81.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4.0 g of 2-benzyl-5-nitroisoindoline prepared in Reference Example 2-(2) was dissolved in 40 ml of methanol and 800 mg of 10% palladium on carbon was added to the solution. The catalytic hydrogenation was performed for 32 hours at room temperature and under atmospheric pressure. After removing the catalyst by filtration, the filtrate was concentrated to obtain 2.88 g of 2-benzyl-5-aminoisoindoline.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e57fabad950d454c8eee0c892aefd3dc
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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