2-Methyl-2-(5-nitropyridin-2-yl)propanenitrile → 2-(5-Aminopyridin-2-yl)-2-methylpropanenitrile

HRID 2174946Notes

Reaction equation

HRID 2174946 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][N:7]=1)([CH3:5])[C:3]#[N:4]>[Ni]>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])=[N:7][CH:8]=1

Participants

3

Reactant 1

HCID 532174502-Methyl-2-(5-nitropyridin-2-yl)propanenitrile

Product 1

HCID 533931752-(5-Aminopyridin-2-yl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

2-methyl-2-(5-nitropyridin-2-yl)propanenitrile (15.70 mmol) was subjected to hydrogenation using Raney-Ni (0.6 g) at 40 psi for 4 h. Reaction mixture was filtered and washed with methanol. Filtrate was concentrated and purified (silica gel column, MeOH/CHCl3 as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 8.11 (d, J=2.7 Hz, 1H), 7.37 (d, J=8.7 Hz, 1H), 7.03 (dd, J=2.7, 8.7 Hz, 1H), 3.36 (brs, 2H), 1.74 (s, 6H); MS m/z: 162 (M+1)+.

Workup

  1. customfor 4 h
  2. customReaction mixture
  3. filtrationwas filtered
  4. washwashed with methanol
  5. concentrationFiltrate was concentrated
  6. custompurified (silica gel column, MeOH/CHCl3 as eluent)

Sources & evidence

ORD record
ord-3cd61540143b4b4ca9fb72b3411cf450
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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