2-Methoxyaniline → N-(2-Methoxyphenyl)glycine ethyl ester

HRID 724836Notes

Reaction equation

HRID 724836 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 70002-MethoxyanilineHCID 7748Ethyl bromoacetate

Product 1

HCID 19711182N-(2-Methoxyphenyl)glycine ethyl esterYield 40.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a cooled (0° C.) solution of 2-methoxyaniline (13.2 g, 0.108 mol) in CHCl3 (100 mL) was added ethyl bromoacetate (6 mL, 0.05 mol) and the mixture was stirred at room temperature overnight. The resulting solution was washed with 0.5N NaOH and the organic phase was concentrated to a crude product. This was purified by chromatography on silica gel (hexane-EtOAc, 10%) to afford ethyl N-(2-methoxyphenyl)aminoacetate (4.2 g, 40%). This compound was dissolved in MeOH (80 mL), a solution of K2CO3 (4.4 g) in H2O (50 mL) was added and the mixture was refluxed overnight. MeOH was removed and the resulting aqueous solution was extracted with hexane. The aqueous phase was acidified with 5N HCl and extracted with CHCl3 (3×). Evaporation of the solvent afforded the title compound.

Workup

  1. washThe resulting solution was washed with 0.5N NaOH
  2. concentrationthe organic phase was concentrated to a crude product
  3. customThis was purified by chromatography on silica gel (hexane-EtOAc, 10%)

Sources & evidence

ORD record
ord-618b18ffd95e43e580833656f241bfb3
Source dataset
uspto-grants-1998_01
Patent number
US05705504

Reaction notes

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