Aniline → N-Phenylglycine ethyl ester

HRID 1583246Notes

Reaction equation

HRID 1583246 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(OCC)C>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:14]

Participants

6

Reactant 3

HCID 6115AnilineHCID 7748Ethyl bromoacetateHCID 517045Sodium Acetate

Product 1

HCID 75190N-Phenylglycine ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Aniline (0.096 mole), ethyl bromoacetate (0.096 mole) and sodium acetate (0.096 mole) in ethanol (150 ml) were refluxed for four hours and stirred at room temperature for 18 hours. The ethanol was removed by a rotary evaporator to give an oil. The oil was dissolved in ethyl ether (200 ml), filtered and the solvent removed by a rotary evaporator. The dark oily residue crystallized from cold hexane. Structural assignment was supported by NMR and the compound is used as is to prepare title compound of Example 1.

Workup

  1. customThe ethanol was removed by a rotary evaporator
  2. customto give an oil
  3. filtrationfiltered
  4. customthe solvent removed by a rotary evaporator
  5. customThe dark oily residue crystallized from cold hexane
  6. customto prepare title compound of Example 1

Sources & evidence

ORD record
ord-f85d3c4ce58943df90a0d0d674e0b8e8
Source dataset
uspto-grants-1985_11
Patent number
US04551279

Reaction notes

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