Hydrochloric Acid → Methyl 3-(3-(aminomethyl)phenyl)propanoate hydrochloride

HRID 2117615

Reaction equation

HRID 2117615 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=1.[ClH:15]>[Pd].CO>[ClH:15].[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH2:13])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53396017Methyl 3-(3-cyanophenyl)prop-2-enoate

Product 1

HCID 22282736Methyl 3-(3-(aminomethyl)phenyl)propanoate hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(3-cyano-phenyl)-acrylic acid methyl ester of Step B (1.37 g, 7.32 mmol), 10% palladium on carbon (1.0 g), and HCl (4N in dioxane, 3 mL) in MeOH (50 mL) was hydrogenated on a Parr shaker at 50 psi for 65 h. The catalyst was removed by filtration through Celite and the solution was concentrated to provide the title compound (1.97 g). 1H NMR (400 MHz, CD3OD) δ 7.35-7.24 (m, 4H), 4.06 (s, 2H), 3.60 (s, 3H), 2.92 (t, 2H), 2.64 (t, 2H).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-52363373f5684974981a0b5e4625e536
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Linked notes

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