Methyl (4-cyanophenyl)acetate → Methyl 4-aminomethylphenylacetate
Reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1>[OH-].[Pd+2].[OH-].[OH-].[NH4+].CO>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Palladium hydroxide (Pearlman's catalyst, 1.04 g) was added to a solution of conc. aq. ammonium hydroxide:methanol (1:4) (50 mL) in a Parr flask. (4-Cyano-phenyl)-acetic acid methyl ester (1.00 g) was added to the solution. The Parr flask was then shaken for 20 min under hydrogen (50 psi). The reaction mixture was filtered (nylon 66) and the filtrate concentrated in vacuo to yield crude title compound (1.22 g).
Workup
- filtrationThe reaction mixture was filtered (nylon 66)
- concentrationthe filtrate concentrated in vacuo
Sources & evidence
- ORD record
- ord-ffe9657b1a10466a9d113f8bb333bf5b
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250518B2
Reaction notes
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