2-amino-4-methylfuran-3-carbonitrile

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4.0 g of 2-amino-3-cyano-4-methylfuran, 3 cc of triethylorthoformate, and 0.05 cc of acetic anhydride was heated to 135° C. for three hours. Then 5 g of 2-(4-chlorophenyl)ethylamine, 5 cc of glacial acetic acid, and 3.2 g of sodium acetate were added to the reaction mixture. The temperature of the mixture was maintained at 135° C. for three additional hours, after which the mixture was cooled, treated with water and extracted with dichloromethane. The organic phase was then concentrated and washed with water. The solids were extracted from the organic phase with large volumes of ether, which were combined and concentrated to provide 1.07 g of product. M. P. 140° C. The temperature of the mixture was maintained at 135° C. for three additional hours after which the mixture was cooled extracted with dichloromethane The organic phase was then concentrated washed with water The solids were extracted from the organic phase with large volumes of ether, which concentrated

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4 g of 2-amino-3-cyano-4-methylfuran, 3 mL of triethylorthoformate and 0.5 mL of acetic anhydride was heated at 135° C. for three hours. To the hot solution was added 4.5 g of 2-(4-methoxyphenyl)ethylamine, 5 mL of acetic anhydride, and 3.1 g of sodium acetate. The temperature of the mixture was kept at 135° C. for three additional hours, then the mixture was cooled and combined with a mixture of water and ether. The ether layer was separated, and product was extracted from the remaining aqueous layer with large volumes of ether. The ether extracts were combined, dried over magnesium sulfate, filtered, and concentrated. The residue was recrystallized from acetone/ether. Yield 2.6 g. M.P. 184° C. was kept at 135° C. for three additional hours the mixture was cooled The ether layer was separated product was extracted from the remaining aqueous layer with large volumes of ether dried over magnesium sulfate filtered concentrated The residue was recrystallized from acetone/ether

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4.0 g of 2-amino-3-cyano-4-methylfuran, 3 cc of triethylorthoformate, and 0.05 cc of acetic anhydride was heated to 135° C. for three hours. Then 5 g of 2-(4-chlorophenyl)ethylamine, 5 cc of glacial acetic acid, and 3.2 g of sodium acetate were added to the reaction mixture. The temperature of the mixture was maintained at 135° C. for three additional hours, after which the mixture was cooled, treated with water and extracted with dichloromethane. The organic phase was then concentrated and washed with water. The solids were extracted from the organic phase with large volumes of ether, which were combined and concentrated to provide 1.07 g of product. M.P. 140° C. The temperature of the mixture was maintained at 135° C. for three additional hours after which the mixture was cooled extracted with dichloromethane The organic phase was then concentrated washed with water The solids were extracted from the organic phase with large volumes of ether, which concentrated

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4.0 g of 2-amino-3-cyano-4-methylfuran, 3 cc of triethylorthoformate, and 0.05 cc of acetic anhydride was heated to 135° C. for three hours. Then 5 g of 2-(4-chlorophenyl)ethylamine, 5 cc of glacial acetic acid, and 3.2 g of sodium acetate were added to the reaction mixture. The temperature of the mixture was maintained at 135° C. for three additional hours, after which the mixture was cooled, treated with water and extracted with dichloromethane. The organic phase was then concentrated and washed with water. The solids were extracted from the organic phase with large volumes of ether, which were combined and concentrated to provide 1.07 g of product. M. P. 140° C. The temperature of the mixture was maintained at 135° C. for three additional hours after which the mixture was cooled extracted with dichloromethane The organic phase was then concentrated washed with water The solids were extracted from the organic phase with large volumes of ether, which concentrated

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4 g of 2-amino-3-cyano-4-methylfuran, 3 mL of triethylorthoformate and 0.5 mL of acetic anhydride was heated at 135° C. for three hours. To the hot solution was added 4.5 g of 2-(4-methoxyphenyl)ethylamine, 5 mL of acetic anhydride, and 3.1 g of sodium acetate. The temperature of the mixture was kept at 135° C. for three additional hours, then the mixture was cooled and combined with a mixture of water and ether. The ether layer was separated, and product was extracted from the remaining aqueous layer with large volumes of ether. The ether extracts were combined, dried over magnesium sulfate, filtered, and concentrated. The residue was recrystallized from acetone/ether. Yield 2.6 g. M.P. 184° C. was kept at 135° C. for three additional hours the mixture was cooled The ether layer was separated product was extracted from the remaining aqueous layer with large volumes of ether dried over magnesium sulfate filtered concentrated The residue was recrystallized from acetone/ether

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

Procedure: To a mixture of malononitrile (0.96 g, 14.6 mmol), acetol (1.08 g, 14.6 mmol) in methanol (10 mL) at 0° C. was added, dropwise, triethylamine (2.0 mL). The reaction mixture was stirred at room temperature overnight. After removal of solvent under reduced pressure the crude solid washed with cold isopropanol to give product as white powder (0.54 g, 30%). HPLC/MS: (M+H)+ 123.3 m/z. Retention time (LC-MS)=1.81 min. 1H NMR (CD3OD): 6.58(s, 1H,); 1.95 (s, 3H). was added After removal of solvent under reduced pressure the crude solid washed with cold isopropanol

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4.0 g of 2-amino-3-cyano-4-methylfuran, 3 cc of triethylorthoformate, and 0.05 cc of acetic anhydride was heated to 135° C. for three hours. Then 5 g of 2-(4-chlorophenyl)ethylamine, 5 cc of glacial acetic acid, and 3.2 g of sodium acetate were added to the reaction mixture. The temperature of the mixture was maintained at 135° C. for three additional hours, after which the mixture was cooled, treated with water and extracted with dichloromethane. The organic phase was then concentrated and washed with water. The solids were extracted from the organic phase with large volumes of ether, which were combined and concentrated to provide 1.07 g of product. M.P. 140° C. The temperature of the mixture was maintained at 135° C. for three additional hours after which the mixture was cooled extracted with dichloromethane The organic phase was then concentrated washed with water The solids were extracted from the organic phase with large volumes of ether, which concentrated

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4.0 g of 2-amino-3-cyano-4-methylfuran, 3 cc of triethylorthoformate, and 0.05 cc of acetic anhydride was heated to 135° C. for three hours. Then 5 g of 2-(4-chlorophenyl)ethylamine, 5 cc of glacial acetic acid, and 3.2 g of sodium acetate were added to the reaction mixture. The temperature of the mixture was maintained at 135° C. for three additional hours, after which the mixture was cooled, treated with water and extracted with dichloromethane. The organic phase was then concentrated and washed with water. The solids were extracted from the organic phase with large volumes of ether, which were combined and concentrated to provide 1.07 g of product. M. P. 140° C. The temperature of the mixture was maintained at 135° C. for three additional hours after which the mixture was cooled extracted with dichloromethane The organic phase was then concentrated washed with water The solids were extracted from the organic phase with large volumes of ether, which concentrated

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4 g of 2-amino-3-cyano-4-methylfuran, 3 mL of triethylorthoformate and 0.5 mL of acetic anhydride was heated at 135° C. for three hours. To the hot solution was added 4.5 g of 2-(4-methoxyphenyl)ethylamine, 5 mL of acetic anhydride, and 3.1 g of sodium acetate. The temperature of the mixture was kept at 135° C. for three additional hours, then the mixture was cooled and combined with a mixture of water and ether. The ether layer was separated, and product was extracted from the remaining aqueous layer with large volumes of ether. The ether extracts were combined, dried over magnesium sulfate, filtered, and concentrated. The residue was recrystallized from acetone/ether. Yield 2.6 g. M.P. 184° C. was kept at 135° C. for three additional hours the mixture was cooled The ether layer was separated product was extracted from the remaining aqueous layer with large volumes of ether dried over magnesium sulfate filtered concentrated The residue was recrystallized from acetone/ether