2-((4-Methoxybenzyl)amino)isonicotinonitrile → (4-Aminomethyl-pyridin-2-yl)-(4-methoxy-benzyl)-amine

HRID 887634Notes

Reaction equation

HRID 887634 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][N:16]=2)[C:12]#[N:13])=[CH:5][CH:4]=1>CCO.[Pd]>[NH2:13][CH2:12][C:11]1[CH:14]=[CH:15][N:16]=[C:9]([NH:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][CH:17]=2)[CH:10]=1

Participants

4

Reactant 1

HCID 219613782-((4-Methoxybenzyl)amino)isonicotinonitrile

Product 1

HCID 21961478(4-Aminomethyl-pyridin-2-yl)-(4-methoxy-benzyl)-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-Methoxy-benzylamino)-isonicotinonitrile (12 g, 50 mmole) was dissolved in a mixed solvent of EtOH (800 mL) Et3N (200 mL) and suspended with 2 g of Pd/C (10%). After removing air with vacuum, the flask was charged with H2 with a balloon. The H2 balloon was refilled every morning and evening. Pd/C was recharged twice (1.3 g each) on days 2 and 3. Reaction was completed on the 4th day and the reaction mixture was filtered through a pad of Celite®. The filter cake was rinsed with MeOH and the combined filtrate was concentrated in vacuo to give the desired compound as a light brown solid.

Workup

  1. customAfter removing air with vacuum
  2. additionthe flask was charged with H2 with a balloon
  3. additionThe H2 balloon was refilled every morning and evening
  4. customReaction
  5. filtrationthe reaction mixture was filtered through a pad of Celite®
  6. washThe filter cake was rinsed with MeOH
  7. concentrationthe combined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-28cf3d4ae8ea48e7a6500c3a847b8a86
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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