2-(4-Nitrobenzyl)pyridine → 2-(4-Aminobenzyl)pyridine

HRID 1277158Notes

Reaction equation

HRID 1277158 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 692922-(4-Nitrobenzyl)pyridine

Product 1

HCID 4595252-(4-Aminobenzyl)pyridineYield 84.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-(4-nitrobenzyl)pyridine (J. Chem. Soc., p549, 1929) (1.50 g) and 5% Pd-C (0.15 g) in ethanol (30 ml) was vigorously stirred under hydrogen atmosphere for 8 hours, and the Pd-C was filtered off. The filtrate was concentrated under reduced pressure, and the residue was separated and purified with column chromatography (ethyl acetate/hexane=1:1→2:1) to give 2-(4-aminobenzyl)-pyridine (1.09 g) as yellow oil.

Workup

  1. filtrationthe Pd-C was filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was separated
  4. custompurified with column chromatography (ethyl acetate/hexane=1:1→2:1)

Sources & evidence

ORD record
ord-f944ba23e7f14d6d9046282da0699aea
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

Loading…