5-ethyl-9-nitro-5H-phenanthridin-6-one → 9-amino-5-ethyl-5H-phenanthridin-6-one

HRID 968281Notes

Reaction equation

HRID 968281 reaction equation
[CH2:1]([N:3]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][C:12]([N+:18]([O-])=O)=[CH:13][CH:14]=2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2)[CH3:2]>C(O)C.[Pd]>[NH2:18][C:12]1[CH:11]=[C:10]2[C:15]([C:16](=[O:17])[N:3]([CH2:1][CH3:2])[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=32)=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 222885445-ethyl-9-nitro-5H-phenanthridin-6-one

Product 1

HCID 103993089-amino-5-ethyl-5H-phenanthridin-6-oneYield 52.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-ethyl-9-nitro-5H-phenanthridin-6-one (5.4 g, 20 mmol) in ethyl alcohol (400 ml) was charged with 10% palladium on activated carbon (500 mg). The resultant suspension was placed on a Parr hydrogenation apparatus and shaken under 50 psi H2 for 18 hours. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to afford 9-amino-5-ethyl-5H-phenanthridin-6-one (2.5 g, quantitative).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4606a39542ef40819334210c3cee1284
Source dataset
uspto-grants-2005_10
Patent number
US06958347B2

Reaction notes

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