3-Cyanopyridine → 2,4-difluoro-N-(pyridin-3-ylmethyl)aniline

HRID 21704

Reaction equation

HRID 21704 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[F:9][C:10]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:11]=1N.[H][H]>[Rh]>[F:9][C:10]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:11]=1[NH:2][CH2:1][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 793-CyanopyridineHCID 97092,4-DifluoroanilineHCID 178418361HCID 178418361, compound3×

Product 1

HCID 110961292,4-difluoro-N-(pyridin-3-ylmethyl)aniline

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

A mixture of 3-cyanopyridine (10.4 g), 2,4-difluoroaniline (129.1 g) and a 5% rhodium on carbon catalyst (1.0 g) was treated with hydrogen at 60 psig and 25-30 deg C. until two equivalents of hydrogen had reacted. The hydrogen pressure was incrementally increased to 400 psig during the course of the reaction. After cooling, venting and pursing with nitrogen, the catalyst was removed by filtration. The filtrate analyzed and found to contain 10.4 g of N-(2,4-diflourophenyl)-N-(3-pyridylmethyl)amine which could be isolated by distillation (158-164 deg. C. @ 3 mm Hg) and recrystallization (cyclohexane) to give a white solid with a melting point of 88.5-90 deg C.

Workup

  1. temperatureAfter cooling
  2. customthe catalyst was removed by filtration
  3. customcould be isolated by distillation (158-164 deg. C. @ 3 mm Hg) and recrystallization (cyclohexane)
  4. customto give a white solid with a melting point of 88.5-90 deg C

Sources & evidence

ORD record
ord-3679422880c241a4bc426a83ff78fa08
Source dataset
uspto-grants-1995_06
Patent number
US05424436

Linked notes

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