N,N-dimethyl-3-(6-methyl-5-nitropyridin-3-yl)prop-2-yn-1-amine → 5-[3-(Dimethylamino)propyl]-2-methylpyridin-3-amine
Reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][C:4]#[C:5][C:6]1[CH:7]=[N:8][C:9]([CH3:15])=[C:10]([N+:12]([O-])=O)[CH:11]=1>CCO.[Ni]>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([NH2:12])[C:9]([CH3:15])=[N:8][CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N,N-dimethyl-3-(6-methyl-5-nitropyridin-3-yl)prop-2-yn-1-amine (3.18 g, 13.8 mmol) in EtOH (50 mL) under an atmosphere of N2 was added Raney 2800 nickel (50% water slurry; 760 mg, 4 mmol) using 5 mL of ethanol to transfer. The mixture was purged with H2 (1 atm) and allowed to stir at rt under an atmosphere of N2 for 20 h. More Raney nickel (620 mg, 3.6 mmol) was added using 5 mL of ethanol to transfer. The mixture was purged with H2 (1 atm) and allowed to stir at rt under an atmosphere of H2 for 20 h. The mixture was filtered through Celite® and the filtrate was concentrated to give 5-[3-(dimethylamino)propyl]-2-methylpyridin-3-amine (2.45 g, 93%) as a brown solid. LCMS (AAL): Rt=0.98 min, m/z=194.4 (M+H).