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

HRID 2388005Notes

Reaction equation

HRID 2388005 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-e5b447668d3b402d92bc27af42bc3ddb
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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