methyl (E)-3-(4-cyanophenyl)prop-2-enoate → Methyl 3-[4-(aminomethyl)phenyl]propionate

HRID 733515Notes

Reaction equation

HRID 733515 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[N:2].[H][H]>CO.[Pd]>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 11106082methyl (E)-3-(4-cyanophenyl)prop-2-enoateHCID 178418361HCID 178418361, compound

Product 1

HCID 413297Methyl 3-[4-(aminomethyl)phenyl]propionateYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To solution of methyl (2E)-3-(4-cyanophenyl)acrylate (18 g, 0.096 mol) in methanol (200 ml) was added Pd/C (1.8 g) and hydrogenated under a pressure of 50 psi of hydrogen for 12 h. The catalyst was filtered off and the filtrate was concentrated to a residue. The residue was purified by chromatography (SiO2, chloroform/methanol 9/1) to yield the title compound as a liquid (16 g, 86%). TLC:CHCl3/MeOH (9/1); Rf: 0.3

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to a residue
  3. customThe residue was purified by chromatography (SiO2, chloroform/methanol 9/1)

Sources & evidence

ORD record
ord-2ea01e9fffbd4663b5c8836741363a7e
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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