Aniline → N-Phenylglycine ethyl ester

HRID 862982Notes

Reaction equation

HRID 862982 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-eb14cf8148e3445b8008b5feb3059c25
Source dataset
uspto-grants-1998_02
Patent number
US05719290

Reaction notes

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