Aniline → N-Phenylglycine ethyl ester

HRID 1600425Notes

Reaction equation

HRID 1600425 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 (8.1g, 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 wassupported 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-db6775655022435fb064f54405ba19d2
Source dataset
uspto-grants-1998_04
Patent number
US05744631

Reaction notes

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