HCID 265049, compound → 3-aminophenanthridin-6(5h)-one

HRID 1604785Notes

Reaction equation

HRID 1604785 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[C:13]([C:14](=[O:18])[NH:15][C:16]=2[CH:17]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3)([O-])=O>CN(C=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[C:13]([C:14](=[O:18])[NH:15][C:16]=2[CH:17]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

4

Reactant 1

HCID 265049HCID 265049, compound

Product 1

HCID 2690393-aminophenanthridin-6(5h)-oneYield 126.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-nitro-6(5H)-phenanthridinone (structure 55 of Scheme XVI, where R1 =H, R2 =R3 =benzo, Y=NH) (480 mg, 1.5 mmol) and 50 mg of 10% Pd/C in 60 mL of DMF was stirred under an atmosphere of H2 for 2 h. The mixture was filtered through a Celite™ pad and the filtrate was concentrated to give 0.4 g of the crude aniline as a yellow solid. This material was used without further purification.

Workup

  1. filtrationThe mixture was filtered through a Celite™ pad
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1e72f774d50b44429468aede9b67df8d
Source dataset
uspto-grants-1999_11
Patent number
US05994544

Reaction notes

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