2-(Methylamino)pyridine-4-carbonitrile → (4-Aminomethyl-pyridin-2-yl)-methyl-amine

HRID 887637Notes

Reaction equation

HRID 887637 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][N:10]=1)[C:6]#[N:7]>CCO.[Pd]>[NH2:7][CH2:6][C:5]1[CH:8]=[CH:9][N:10]=[C:3]([NH:2][CH3:1])[CH:4]=1

Participants

4

Reactant 1

HCID 219614802-(Methylamino)pyridine-4-carbonitrile

Product 1

HCID 62104719(4-Aminomethyl-pyridin-2-yl)-methyl-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-Methylamino-isonicotinonitrile (5.6 g) and Pd/C (10%, 4 g) in EtOH (150 mL) and TEA (40 mL) was placed in a 500 mL Parr Hydrogenation bottle and hydrogenated at or below 60 psi H2 pressure over night. After filtering through a pad of Celite®, the reaction mixture was concentrated in vacuo to give a yellow oil as the desired compound.

Workup

  1. waithydrogenated at or below 60 psi H2 pressure over night
  2. filtrationAfter filtering through a pad of Celite®
  3. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-2460f7546b4e43cf8f1654f8fc47b63b
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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