Dimethylformamide → Ethyl 2-(2-cyanoanilino)acetate

HRID 1728404Notes

Reaction equation

HRID 1728404 reaction equation
[C:1]([NH2:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].CN(C)C=O>O>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]#[N:10])[CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6942AnthranilamideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 2779716Ethyl 2-(2-cyanoanilino)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of anthranilamide (11.8 g), potassium carbonate (20 g), ethyl bromoacetate (18 g) and dimethylformamide (50 mL) was heated at reflux for 40 min. The reaction mixture was diluted with water and the product was extracted with ether. The organic layer was washed with water and brine, dried over magnesium sulfate and the solvent was removed in vacuo. The residue was recrystallized from ethanol to afford N-(2-Cyanophenyl)glycine ethyl ester as a colorless solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 40 min
  3. extractionthe product was extracted with ether
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-98bc41b188784cc3baca6075de8ed82d
Source dataset
uspto-grants-1994_07
Patent number
US05326868

Reaction notes

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