N-[2-(5-nitro-1H-indol-3-yl)ethyl]acetamide → N-[2-(5-Amino-1H-indol-3-yl)ethyl]acetamide

HRID 1581716Notes

Reaction equation

HRID 1581716 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17]

Participants

4

Reactant 1

HCID 906605N-[2-(5-nitro-1H-indol-3-yl)ethyl]acetamide

Product 1

HCID 22722278N-[2-(5-Amino-1H-indol-3-yl)ethyl]acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product from Example 2 (0.05 mmol) is taken into ethanol (3 mL) and hydrogenated 6 h at 3 atmospheres of H2 pressure over a catalytic amount of 10% Pd/C. The catalyst is removed by filtration through Celite and the solvent removed in vacuo, affording the title compound. This product is somewhat air sensitive and is used immediately for subsequent reactions.

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3d06ed28c8df4b51a5d3ea72070d9562
Source dataset
uspto-grants-2004_05
Patent number
US06730707B2

Reaction notes

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