2-(4-Nitrophenyl)propiononitrile → 2-(4-Aminophenyl)propiononitrile
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:13])[C:11]#[N:12])=[CH:6][CH:5]=1)([O-])=O>[C].[Pd].C1COCC1.CCO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:13])[C:11]#[N:12])=[CH:8][CH:9]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To the flask was added THF/EtOH (1:1, 70 mL) followed by 2-(4-nitrophenyl)-propionitrile (13.2 g, 74.9 mmol) and 10% palladium carbon (1.07 g) at room temperature. The reaction mixture was hydrogenated and stirred for 30 minutes at 47 psi to 28 psi then filtered through celite bed, and washed with EtOAc. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:3) as eluant.
Workup
- filtrationthen filtered through celite bed
- washwashed with EtOAc
- concentrationThe filtrate was concentrated in vacuo
- customThe residue was purified by flash column chromatography on silica gel
Sources & evidence
- ORD record
- ord-22174395b9b44522b5d27eb1656ec346
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084484B2
Reaction notes
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