3,4-Dimethylaniline → Glycine, N-(3,4-dimethylphenyl)-, methyl ester

HRID 703800Notes

Reaction equation

HRID 703800 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].Br[CH2:11][C:12]([O:14][CH3:15])=[O:13]>CCOCC>[CH3:15][O:14][C:12](=[O:13])[CH2:11][NH:5][C:4]1[CH:6]=[CH:7][C:8]([CH3:9])=[C:2]([CH3:1])[CH:3]=1

Participants

4

Reactant 2

HCID 72483,4-DimethylanilineHCID 60984Methyl bromoacetate

Product 1

HCID 785322Glycine, N-(3,4-dimethylphenyl)-, methyl esterYield 81.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3,4-Dimethylaniline (70.0 g) and methyl bromoacetate (44.2 g) were stirred at 100° under nitrogen for 2 h. The cooled reaction mixture was poured into ether (700 ml) and filtered. The collected solid was washed with ether (2×100 ml) and the combined filtrates were concentrated to give a solid (45.6 g) which was purified by FCC on triethylamine deactivated silica eluting with dichloromethane:petroleum ether (1:3) to give a solid (21.8 g), a portion of which (2.5 g) was purified further by FCC as above to give the title compound (2.06 g), m.p. 53°-55°.

Workup

  1. customThe cooled reaction mixture
  2. filtrationfiltered
  3. washThe collected solid was washed with ether (2×100 ml)
  4. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-35c8639a29f5497781a5ef5fc97bc126
Source dataset
uspto-grants-1991_01
Patent number
US04985427

Reaction notes

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