Ethanol → 2-(3,4-Diaminobenzyl)isoindole-1,3-dione

HRID 412689Notes

Reaction equation

HRID 412689 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1[N+:22]([O-])=O)[CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])([O-])=O.C(O)C.C1COCC1>[Pd].C(O)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1[NH2:22])[CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18]

Participants

6

Reactant 3

HCID 702EthanolHCID 8028TetrahydrofuranHCID 185379582-(3,4-Dinitrobenzyl)isoindole-1,3-dione

Product 1

HCID 185377612-(3,4-Diaminobenzyl)isoindole-1,3-dioneYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-(3,4-dinitrobenzyl)isoindole-1,3-dione (8 g, 24.4 mmol), prepared as in Example 1, and 10% palladium on carbon (300 mg) was combined with anhydrous ethanol (200 mL, anhydrous THF (100 mL) and glacial acetic acid (30 mL) under a continuous stream of nitrogen. The mixture then was stirred vigorously 15 hours at room temperature under hydrogen, filtered and concentrated to a volume of approximately 30 mL by rotary evaporation. The mixture was diluted with water (100 mL) and ammonium hydroxide was added to give an orange precipitate. The precipitate was isolated by filtration and washed several times with water to provide 2-(3,4-diaminobenzyl)isoindole-1,3-dione (6 g, 91% yield); 1H-NMR (300 Mhz, DMSO-d6): 7.76-7.85 (m, 4H), 6.31-6.43 (m, 3H), 4.51 (broad s, 4H), 4.47 (s, 2H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to a volume of approximately 30 mL by rotary evaporation
  3. additionThe mixture was diluted with water (100 mL) and ammonium hydroxide
  4. additionwas added
  5. customto give an orange precipitate
  6. customThe precipitate was isolated by filtration
  7. washwashed several times with water

Sources & evidence

ORD record
ord-64c7323aa05c4054832e76807c97b940
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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