HCID 16119276, compound → HCID 16119275, compound

HRID 2105930Notes

Reaction equation

HRID 2105930 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[C:12]3[C:7]2=[C:8]([CH:27]=1)[C:9](=[O:26])[N:10]([CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:11]3=[O:19])([O-])=O>[Pd].CN(C)C=O>[NH2:1][C:4]1[CH:5]=[C:6]2[CH:15]=[C:14]([NH2:16])[CH:13]=[C:12]3[C:7]2=[C:8]([CH:27]=1)[C:9](=[O:26])[N:10]([CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:11]3=[O:19]

Participants

4

Reactant 1

HCID 16119276HCID 16119276, compound

Product 1

HCID 16119275HCID 16119275, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(5,8-Dinitro-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-butyric acid (see example 4; 0.37 g, 1 mmol), palladium on charcoal 10% and dimethylformamide (20 mL) was hydrogenated at room temperature with vigorous stirring for 24 hours. The catalyst was filtered off and the filtrate evaporated under reduced pressure. The residue was crystallized from dimethylformamide and water to give the desired product.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate evaporated under reduced pressure
  4. customThe residue was crystallized from dimethylformamide and water

Sources & evidence

ORD record
ord-5597dad7094b46d4a1c7eedd25d55b45
Source dataset
uspto-grants-2009_08
Patent number
US07579468B2

Reaction notes

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