1h-Isoindol-1-one,2,3-dihydro-5-(4-nitrophenoxy)- → 1h-Isoindol-1-one,5-(4-aminophenoxy)-2,3-dihydro-

HRID 491077Notes

Reaction equation

HRID 491077 reaction equation
[C:1]1(=[O:20])[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=3)=[CH:7][CH:8]=2)[CH2:3][NH:2]1>CCO.[Pd]>[O:20]=[C:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)=[CH:7][CH:8]=2)[CH2:3][NH:2]1

Participants

4

Reactant 1

HCID 231372471h-Isoindol-1-one,2,3-dihydro-5-(4-nitrophenoxy)-

Product 1

HCID 231372161h-Isoindol-1-one,5-(4-aminophenoxy)-2,3-dihydro-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A slurry of 4-(1-isoindolinon-5-yloxy)-1-nitrobenzene (2.12 g, 7.8 mmol) and 10% Pd/C (0.20 g) in EtOH (50 mL) was stirred under an H2 atmosphere (balloon) for 4 h, then filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to afford 4-(1-oxoisoindolin-5-yloxy)aniline as a dark yellow solid: TLC (100% EtOAc) Rf0.15.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1f40193e8cc046509529be72ffe6a86f
Source dataset
uspto-grants-2009_05
Patent number
US07528255B2

Reaction notes

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