ethyl 2-(2-cyanoanilino)acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(2-Cyanophenyl)glycine ethyl ester (8.1 g) in THF (125 mL) was added potassium t-butoxide (4.5 g) in one portion with stirring. After 10 min at room temperature the mixture was diluted with saturated ammonium chloride solution and the product was extracted with ether. After drying, over magnesium sulfate the solvent was removed in vacuo and the residue was recrystallized from 80% methanol to afford 3-Amino-2-carboethoxyindole as a tan solid. the product was extracted with ether After drying, over magnesium sulfate the solvent was removed in vacuo the residue was recrystallized from 80% methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. was heated at reflux for 40 min the product was extracted with ether The organic layer was washed with water and brine dried over magnesium sulfate the solvent was removed in vacuo The residue was recrystallized from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. was heated at reflux for 40 min the product was extracted with ether The organic layer was washed with water and brine dried over magnesium sulfate the solvent was removed in vacuo The residue was recrystallized from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. was heated at reflux for 40 min the product was extracted with ether The organic layer was washed with water and brine dried over magnesium sulfate the solvent was removed in vacuo The residue was recrystallized from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(2-Cyanophenyl)glycine ethyl ester (8.1 g) in THF (125 mL) was added potassium t-butoxide (4.5 g) in one portion with stirring. After 10 min at room temperature the mixture was diluted with saturated ammonium chloride solution and the product was extracted with ether. After drying over magnesium sulfate the solvent was removed in vacuo and the residue was recrystallized from 80% methanol to afford 3-Amino-2-carboethoxyindole as a tan solid. the product was extracted with ether After drying over magnesium sulfate the solvent was removed in vacuo the residue was recrystallized from 80% methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. was heated at reflux for 40 min the product was extracted with ether The organic layer was washed with water and brine dried over magnesium sulfate the solvent was removed in vacuo The residue was recrystallized from ethanol