N,N-dimethyl-3-(6-methyl-5-nitropyridin-3-yl)prop-2-yn-1-amine → 5-[3-(Dimethylamino)propyl]-2-methylpyridin-3-amine

HRID 1892204Notes

Reaction equation

HRID 1892204 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]=1

Participants

4

Reactant 1

HCID 58476572N,N-dimethyl-3-(6-methyl-5-nitropyridin-3-yl)prop-2-yn-1-amine

Product 1

HCID 584766405-[3-(Dimethylamino)propyl]-2-methylpyridin-3-amineYield 93%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent3×

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 H2 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).

Workup

  1. customThe mixture was purged with H2 (1 atm)
  2. customThe mixture was purged with H2 (1 atm)
  3. stirringto stir at rt under an atmosphere of H2 for 20 h
  4. filtrationThe mixture was filtered through Celite®
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-eb859091b0c94f8ea0756587ef9161e0
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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