Methyl (4-cyanophenyl)acetate → Methyl 4-aminomethylphenylacetate

HRID 1297578Notes

Reaction equation

HRID 1297578 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]=1

Participants

4

Reactant 1

HCID 1512619Methyl (4-cyanophenyl)acetate

Product 1

HCID 1514145Methyl 4-aminomethylphenylacetateYield 119.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21894508Ammonium hydroxide methanolSolvent

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

  1. filtrationThe reaction mixture was filtered (nylon 66)
  2. 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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