4-(4-Nitrobenzyl)pyridine → 4-[(Pyridin-4-yl)methyl]aniline

HRID 2110069Notes

Reaction equation

HRID 2110069 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[N:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:16][CH:15]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 141294-(4-Nitrobenzyl)pyridine

Product 1

HCID 3071584-[(Pyridin-4-yl)methyl]anilineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(4-nitrobenzyl)pyridine (7.0 g, 32.68 mmol) in EtOH (200 mL) was added 10% Pd/C (0.7 g) and the resulting slurry was shaken under a H2 atmosphere (50 psi) using a Parr shaker. After 1 h, TLC and 1H-NMR of an aliquot indicated complete reaction. The mixture was filtered through a short pad of Celite®. The filtrate was concentrated in vacuo to afford a white solid (5.4 g, 90%): 1H-NMR (DMSO-d6) δ 3.74 (s, 2H), 4.91 (br s, 2H), 6.48 (d, J=8.46 Hz, 2H), 6.86 (d, J=8.09 Hz, 2H), 7.16 (d, J=5.88 Hz, 2H), 8.40 (d, J=5.88 Hz, 2H); EI-MS m/z 184 (M+). This material was used in urea formation reactions without further purification. A12. General Method for Substituted Aniline Formation via Dissolving Metal Reduction of a Nitroarene

Workup

  1. customreaction
  2. filtrationThe mixture was filtered through a short pad of Celite®
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-23159f424d3042bba3c4249d1e4dd43d
Source dataset
uspto-grants-2009_04
Patent number
US07517880B2

Reaction notes

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