5-Ethyl-2-(2-(4-nitrophenoxy)ethyl)pyridine → 4-[2-(5-Ethyl-2-pyridyl)ethoxy]aniline

HRID 1743335Notes

Reaction equation

HRID 1743335 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]>CO.[Pd]>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 133148065-Ethyl-2-(2-(4-nitrophenoxy)ethyl)pyridine

Product 1

HCID 114997094-[2-(5-Ethyl-2-pyridyl)ethoxy]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(2-(5-ethyl-2-pyridyl)ethoxy)nitrobenzene (23 g) in methanol is hydrogenated under atmospheric pressure in the presence of 10% Pd on carbon (50% humid, 2.5 g). The catalyst is removed by filtering. Distilling the solvent off under reduced pressure gives 4-(2-(5-ethyl-2-pyridyl)ethoxy)aniline as crude oil (20 g, 98%).

Workup

  1. customThe catalyst is removed
  2. filtrationby filtering
  3. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-9f91bea274924d44895df78dabcf5efc
Source dataset
uspto-grants-2006_03
Patent number
US07009057B2

Reaction notes

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