Potassium Hydroxide → 2-(4-Methoxybenzylamino)-4,6-dimethylnicotinamide

Participants

Reaction Conditions

Reaction Steps

In a three-necked flask containing ethanol (6.12mL) is added ethyl 3-amino-3-ethoxyacrylate hydrochloride(3g, 15.3mmol). The solution is treated with 4-methoxybenzylamine(2mL, 15.3mmol) and the mixture is stirred at 22° C. for 1.5 h. The reaction mixture was heated to 80° C. for 3 h. The reaction is cooled to 22° C. and an ethanolic solution of potassium hydroxide (0.86 g, 15.3 mmol, 25.0 mL of ethanol) is added. Neat 2,4-pentanedione (1.57 mL, 15.3 mmol) is added to the solution dropwise over 15 minutes at room temperature. The reaction mixture is aged at room temperature for 24 hours. During the age the nicotinate precipitates out of the reaction as does KCl. The reaction mixture is concentrated in vacuo. The crude mixture is chromatographed on silica gel to afford a 70% yield of the product, ethyl 2-(4-methoxybenzylamino )-4,6-dimethylnicotinate, 27.

Provenance & Evidence