Aniline → N-Phenylglycine ethyl ester

HRID 1449766Notes

Reaction equation

HRID 1449766 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].C([O-])(=O)C.[Na+]>C(O)C>[C:2]1([NH:1][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 7748Ethyl bromoacetateHCID 517045Sodium Acetate

Product 1

HCID 75190N-Phenylglycine ethyl esterYield 3.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of aniline (9.7 g, 104 mmol) and ethyl bromoacetate (16.3 g, 98 mmol) in 150 mL of absolute ethanol was added solid sodium acetate (8.1 g, 99 mmol) in portions. After stirring at room temperature, the solvent was removed by rotary evaporator and the residue suspended in diethyl ether, filtered through Celite and concentrated. Chromatography of the crude residue on silica gel using 20-80 ethyl acetate-hexane as eluant gave the title compound (580 mg) as a light brown solid. The structure was supported by NMR, infrared spectroscopy, elemental analysis, and mass spectroscopy.

Workup

  1. customthe solvent was removed by rotary evaporator
  2. filtrationfiltered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3c718fe349a2454d8470a6c331e66eab
Source dataset
uspto-grants-1997_02
Patent number
US05599947

Reaction notes

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