Ethyl 2-(4-nitro-1H-imidazole-1-yl)octanoate → ethyl 2-(4-amino-1H-imidazol-1-yl)octanoate

HRID 1899413Notes

Reaction equation

HRID 1899413 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:6]1[CH:10]=[C:9]([N+:11]([O-])=O)[N:8]=[CH:7]1)[CH3:2].[H][H]>[Pd]>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:6]1[CH:10]=[C:9]([NH2:11])[N:8]=[CH:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 10062368Ethyl 2-(4-nitro-1H-imidazole-1-yl)octanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 15222343ethyl 2-(4-amino-1H-imidazol-1-yl)octanoateYield 100.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 5.9 g of 4-nitro-α-hexyl-1H-imidazole-1-acetic acid ethyl ester, 3 g of palladium-on-carbon and 150 ml of absolute alcohol were subjected to catalytic hydrogenation. Both theoretical and actual hydrogen uptake was 73 pounds. The catalyst was removed by filtration and the filtrate concentrated in vacuo to provide 5.3 g of the desired title intermediate which was used directly.

Workup

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

Sources & evidence

ORD record
ord-90ae687fcf6b441ab39b5fe2b4a6784c
Source dataset
uspto-grants-1996_11
Patent number
US05571925

Reaction notes

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