3,6-Dimethylpicolinonitrile → (3,6-Dimethylpyridin-2-yl)methanamine

HRID 254157Notes

Reaction equation

HRID 254157 reaction equation
[CH3:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1>CCO.[Ni]>[CH3:1][C:2]1[C:3]([CH2:9][NH2:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 121756763,6-Dimethylpicolinonitrile

Product 1

HCID 22948776(3,6-Dimethylpyridin-2-yl)methanamineYield 99.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 3,6-dimethylpyridine-2-carbonitrile (264 mg, 2.00 mmol) in EtOH (10 mL) was treated with Raney-Ni (approximately 100 mg) and stirred under an atmosphere of hydrogen for 4 h at room temperature. The mixture was filtered through Celite and concentrated in vacuo to give the title compound (270 mg, 99%) as a yellow oil; NMR δH (400 MHz, CDCl3) 2.31 (3H, s), 2.51 (3H, s), 4.17 (2H, s), 7.00 (1H, d, J 7.5 Hz) and 7.37 (1H, d, J 7.5 Hz); M/Z 137 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-adf20956633e444db0ed7d2b3ce78923
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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