3-Cyanopyridine → N-(pyridin-3-ylmethyl)aniline

HRID 21703

Reaction equation

HRID 21703 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].N[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[H][H]>[Rh]>[C:10]1([NH:2][CH2:1][C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 793-CyanopyridineHCID 6115AnilineHCID 178418361HCID 178418361, compound

Product 1

HCID 1082702N-(pyridin-3-ylmethyl)aniline

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

A mixture of 3-cyanopyridine (10.4 g), aniline (101.8 g) and a 5% rhodium on carbon catalyst (1.0 g) was treated with hydrogen at 60 psig 30 deg C. for 13 hours in a rocking autoclave. The catalyst was removed by filtration and the filtrate analyzed by glc to show 3.7 g of N-phenyl-N-(3-pyridylmethyl)amine.

Workup

  1. customThe catalyst was removed by filtration

Sources & evidence

ORD record
ord-2dc1b1df31414fdabba8d25b8bcdf139
Source dataset
uspto-grants-1995_06
Patent number
US05424436

Linked notes

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