5-ethyl-8-nitro-5H-phenanthridin-6-one → 8-amino-5-ethyl-5H-phenanthridin-6-one

HRID 968289Notes

Reaction equation

HRID 968289 reaction equation
[CH2:1]([N:3]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:18]([O-])=O)[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:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:3]([CH2:1][CH3:2])[C:16]2=[O:17]

Participants

4

Reactant 1

HCID 222885455-ethyl-8-nitro-5H-phenanthridin-6-one

Product 1

HCID 222885418-amino-5-ethyl-5H-phenanthridin-6-oneYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-ethyl-8-nitro-5H-phenanthridin-6-one I-16b (100 mg, 0.37 mmol) in ethyl alcohol (25 ml) was charged with 10% palladium on activated carbon (25 mg). The resultant suspension was placed on a Parr hydrogenation apparatus and shaken under 50 psi H2 for 3 hours. The catalyst was removed by filtration through celite, and the filtrate was concentrated in vacuo to afford 8-amino-5-ethyl-5H-phenanthridin-6-one I-16c (74 mg, 84%).

Workup

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

Sources & evidence

ORD record
ord-213b0c8a169049e18e067ccf48b2e7d6
Source dataset
uspto-grants-2005_10
Patent number
US06958347B2

Reaction notes

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