4-(6-Nitropyridin-3-yl)piperazin-2-one → 4-(6-Aminopyridin-3-yl)piperazin-2-one

HRID 592175Notes

Reaction equation

HRID 592175 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][C:12](=[O:16])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][C:12](=[O:16])[CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 584479234-(6-Nitropyridin-3-yl)piperazin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 284115114-(6-Aminopyridin-3-yl)piperazin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a round-bottom flask was added 4-(6-nitropyridin-3-yl)piperazin-2-one 141-3 (0.7 g, 3.1 mmol), Pd/C (0.2 g) and methanol (20 mL). The reaction was stirred for 4 hours under hydrogen atmosphere by attaching a hydrogen balloon. The reaction was flashed with nitrogen and the solid was removed by filtration. The solvent was removed by rotary evaporation to give 4-(6-aminopyridin-3-yl)piperazin-2-one 141-4 as purple solid. MS m/z 193.2 (M+1).

Workup

  1. customthe solid was removed by filtration
  2. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-1a3a63fa56ed43e3944005f8dfbdf0a3
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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