Hydrochloric Acid → Methyl 3-(2-aminoethyl)benzoate

HRID 480331Notes

Reaction equation

HRID 480331 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]#[N:12])[CH:5]=1.Cl>CCO.O=[Pt]=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][NH2:12])[CH:5]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10821136Methyl 3-(cyanomethyl)benzoate

Product 1

HCID 10511548Methyl 3-(2-aminoethyl)benzoateYield 84.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-cyanomethyl-benzoic acid methyl ester (1.36 g) in EtOH (25 mL) was saturated with HCl (g) and PtO2 (200 mg) was added. The reaction was hydrogenated on a Parr shaker at 50 psi for 2.5 h. The catalyst was removed via filtration through Celite and the solvent was removed in vacuo. The resulting solid was stirred in Et2O and the mixture was filtered to yield the title compound as a white solid (1.18 g). MS 180 (M+1).

Workup

  1. additionwas added
  2. customThe catalyst was removed via filtration through Celite
  3. customthe solvent was removed in vacuo
  4. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-5b0d8eada1d5469d983210761aa9d363
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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