2-Methyl-2-(3-nitrophenyl)propanenitrile → 2-(3-Aminophenyl)-2-methylpropanenitrile
Reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1)([CH3:5])[C:3]#[N:4]>CO.[Pd]>[NH2:12][C:8]1[CH:7]=[C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])[CH:11]=[CH:10][CH:9]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Methyl-2-(3-nitrophenyl)-propionitrile (0.5 g) was hydrogenated over 10% Pd—C in methanol (10 ml) at atmospheric pressure until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to oil. Column chromatography over silica gel by eluting with ethyl acetate/pet ether (1:9) gave 2-(3-amino-phenyl)-2-methyl-propionitrile (0.35 g, 83%) as an oil.
Workup
- filtrationThe reaction mixture was then filtered over celite and
- concentrationconcentrated to oil
- washColumn chromatography over silica gel by eluting with ethyl acetate/pet ether (1:9)
Sources & evidence
- ORD record
- ord-50019a57dca74cb8b5b61346fdd62c11
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486962B2
Reaction notes
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