Ammonia → 3-(Aminomethyl)-N,N-dimethylpyridin-2-amine

HRID 1582180Notes

Reaction equation

HRID 1582180 reaction equation
N.[C:2]([C:4]1[C:5]([N:10]([CH3:12])[CH3:11])=[N:6][CH:7]=[CH:8][CH:9]=1)#[N:3]>[Ni].C(O)C>[NH2:3][CH2:2][C:4]1[C:5]([N:10]([CH3:12])[CH3:11])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 122967582-(dimethylamino)nicotinonitrile

Product 1

HCID 167847093-(Aminomethyl)-N,N-dimethylpyridin-2-amineYield 103.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Saturated aqueous ammonia (17 ml) and Raney nickel (3.0 g) were added to a solution of 3-cyano-2-(dimethylamino)pyridine (2.45 g) in ethanol (50 ml) and the mixture was stirred at room temperature for 8 hours under a hydrogen atmosphere of 1 atmospheric pressure. After absorption of 760 ml of hydrogen, the catalyst was removed by filtration. By concentrating the mother liquid, 3-(aminomethyl)-2-(dimethylamino)pyridine (2.61 g) was obtained as a yellow oil.

Workup

  1. customAfter absorption of 760 ml of hydrogen
  2. customthe catalyst was removed by filtration
  3. concentrationBy concentrating the mother liquid

Sources & evidence

ORD record
ord-57386b9d5e3a4196aa51b42ff3010e80
Source dataset
uspto-grants-2004_05
Patent number
US06734203B2

Reaction notes

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