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

HRID 842745Notes

Reaction equation

HRID 842745 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[CH:6]=1.O1CCOCC1.[H][H].[ClH:22]>CO.[Pd]>[ClH:22].[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH2:12])[CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 1514291Methyl (3-cyanophenyl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 21185371Methyl 2-[3-(aminomethyl)phenyl]acetate hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3-cyano-phenyl)-acetic acid methyl ester (18.06 g, 103 mmol) in MeOH (150 mL) and 4M HCl in dioxane (30.0 mL, 120 mmol) was added 10% palladium on carbon (2 g). The mixture was placed on a Parr shaker and was hydrogenated at 50 psi hydrogen for 24 h. The catalyst was removed via filtration through Celite® and the organic solution was concentrated in vacuo. The resulting solid was stirred in EtOAc and filtered to provide the title compound as a white solid (20.42 g). 1H NMR (400 MHz, CD3OD) δ 7.42-7.32 (m, 4H), 4.09 (s, 2H), 3.69 (s, 2H), 3.67 (s, 3H); MS 180 (M+1). mg).

Workup

  1. customThe catalyst was removed via filtration through Celite®
  2. concentrationthe organic solution was concentrated in vacuo
  3. filtrationfiltered

Sources & evidence

ORD record
ord-0cdddc6cb0194e468dc8cad6a88e3039
Source dataset
uspto-grants-2002_04
Patent number
US06376502B1

Reaction notes

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