2-cyano-N-phenylacetamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of 2-cyano-acetanilide (0.801 g, 5.0 mmol) and tri-n-butyltin azide (2.05 mL, 7.5 mmol) in anhydrous toluene (10 mL) was heated at reflux for 48 hrs. The mixture was allowed to cool to room temperature and treated with 2.0 N HCl in Et2O (5.0 mL). The resulting precipate was collected by suction, washed with hexane and dried in vacuo to give 2-(1H-tetrazol-5-yl)acetanilide (0.917 g, 90%) as a white solid. at reflux for 48 hrs The resulting precipate was collected by suction washed with hexane dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of 8-hydroxy-5-quinolinecarboxaldehyde (1.732 g, 0.010 mol), N-phenyl cyanoacetamide (1.602 g, 0.010 mol) and piperidine (0.255 g, 0.003 mol) in absolute ethanol (50 ml) was heated for 3 h at reflux. The reaction mixture was chilled to about 10°-15° C., the precipitate filtered, the residue washed with ice-cooled ethanol and dried under vacuum. Almost pure title compound was obtained in about 75% yield (2.365 g). at reflux The reaction mixture was chilled to about 10°-15° C. the precipitate filtered the residue washed with ice- cooled ethanol dried under vacuum

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

Procedure: A solution of 8-hydroxy-5-quinolinecarboxaldehyde (1.732 g, 0.010 mol), N-phenyl cyanoacetamide (1.602 g, 0.010 mol) and piperidine (0.255 g, 0.003 mol) in absolute ethanol (50 ml) was heated for 3 h at reflux. The reaction mixture was chilled to about 10°-15° C., the precipitate filtered, the residue washed with ice-cooled ethanol and dried under vacuum. Almost pure title compound was obtained in about 75% yield (2.365 g). at reflux The reaction mixture was chilled to about 10°-15° C. the precipitate filtered the residue washed with ice- cooled ethanol dried under vacuum

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

Procedure: to a solution of 1.6 g of α-cyanoacetanilide in 10 ml of dimethylformamide is added 3.4 g of potassium t-butoxide. The stirred cooled suspension is treated with a solution of 1.1 g of pyrrole-2-carboxylic acid and 1.4 ml of diethyl phosphorocyanidate in 6 ml of dimethylformamide. After standing for one half hour, solution is treated with 80 ml of cold water, filtered and acidified with 6N hydrochloric acid. The suspended product is collected, washed with water, dried, and dissolved in ethyl acetate. The ethyl acetate solution is filtered and evaporated to dryness. Recrystallization from ether-ethanol yields β-oxo-α-(phenylcarbamoyl)-β-(2-pyrrolyl)-propionitrile of Example 1. The stirred cooled suspension After standing for one half hour filtered The suspended product is collected washed with water dried dissolved in ethyl acetate The ethyl acetate solution is filtered evaporated to dryness Recrystallization from ether-ethanol

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

Procedure: A 10.0 g. amount of 2-cyanoacetanilide in 25 ml. of N,N-dimethylformamide dimethylacetal is heated on a steam bath for 2-6 hours. The reaction mixture volatiles are removed in vacuo and the resultant solid is dissolved in dichloromethane. The solution is passed through a short column of hydrous magnesium silicate, then n-hexane is added to the effluent until crystallization is noted. After cooling, the product is collected by filtration to give 2-cyano-3-dimethylamino-acrylanilide as colorless plates, m.p. 162.5°-164° C. The reaction mixture volatiles are removed in vacuo the resultant solid is dissolved in dichloromethane n-hexane is added to the effluent until crystallization After cooling the product is collected by filtration

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

Procedure: Following the procedure as set forth in Example 6 above, N-phenylcyanoacetamide was condensed with 3,4-dihydroxybenzaldehyde to yield the title compound, m.p. 258° C.

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

Procedure: Following the procedure as set forth in Example 6 above, N-phenylcyanoacetamide was condensed with 3,4-dihydroxybenzaldehyde to yield the title compound, m.p. 258° C.