1H-Isoindole-1,3(2H)-dione, 2-(2-nitrophenyl)- → 2-(2-Aminophenyl)isoindole-1,3-dione

HRID 1836429

Reaction equation

HRID 1836429 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])([O-])=O>C1C=CC=CC=1>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:11](=[O:20])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]1=[O:19]

Participants

3

Reactant 1

HCID 1013131H-Isoindole-1,3(2H)-dione, 2-(2-nitrophenyl)-

Product 1

HCID 6736762-(2-Aminophenyl)isoindole-1,3-dioneYield 40%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of the 2-(2-nitrophenyl)isoindole-1,3-dione (1.0 g, 3.50 mmol) in benzene, pre-sparged with nitrogen gas, was added 10% palladium on activated carbon (1.0 g). The reaction mixture was placed under an atmosphere of hydrogen gas and was vigorously stirred. After 45 minutes, the reaction mixture was filtered over celite and the filter pad was washed with benzene. Concentration in vacuo gave 236 mg (40%) of 2-(2-aminophenyl)-isoindole-1,3-dione as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 8.85 (m, 4H), 7.10 (m, 1H), 6.98 (m, 1H), 6.75 (m, 1H), 6.55 (m, 1H).

Workup

  1. custompre-sparged with nitrogen gas
  2. additionwas added 10% palladium on activated carbon (1.0 g)
  3. filtrationthe reaction mixture was filtered over celite
  4. washthe filter pad was washed with benzene
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-0c75ce1b22c946ea89fb0c570c4d3a2c
Source dataset
uspto-grants-2004_08
Patent number
US06777432B1

Linked notes

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