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

HRID 890791Notes

Reaction equation

HRID 890791 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-a1ef69dadf7d449b854cec8f009345bf
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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