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

HRID 1672214Notes

Reaction equation

HRID 1672214 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 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).

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-a054a0fc867a41cea0bea9e89f09fb7f
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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