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

HRID 1387912Notes

Reaction equation

HRID 1387912 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-1c7474b3669d496587bc4792e1213229
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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