Hydrochloric Acid → Ethyl 2-[3-(aminomethyl)phenyl]acetate

HRID 480309Notes

Reaction equation

HRID 480309 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=1)[CH3:2].Cl.O1CCOCC1>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH2:13])[CH:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 11194802Ethyl 2-(3-cyanophenyl)acetate

Product 1

HCID 53425498Ethyl 2-[3-(aminomethyl)phenyl]acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent3×

Procedure

A solution of (3-cyano-phenyl)-acetic acid ethyl ester (6.3 g, 33.29 mmol) in EtOH (50 mL) was added to a mixture of 10% Pd/C (1.26 g) in EtOH (50 mL) under Nitrogen. Additional EtOH (150 mL) was added followed by a solution of HCl in dioxane (4M, 11.4 mL, 45.6 mmol). The mixture was hydrogenated on a Parr shaker at 45 psi for 20 h and the catalyst was removed by filtration through celite. The solution was concentrated to afford (3-aminomethyl-phenyl)-acetic acid ethyl ester as the hydrochloride salt (7.31 g). 1H NMR (400 MHz, CD3OD) δ 7.42-7.32 (m, 4H), 4.12 (q, 2H), 4.09 (s, 2H), 3.68 (s, 2H), 1.23 (t, 3H).

Workup

  1. customthe catalyst was removed by filtration through celite
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-46184bbb11cc43ba8770555e91f96830
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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