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

Temperature

22 °C

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.

1. temperatureThe reaction mixture was heated to 80° C. for 3 h
2. temperatureThe reaction is cooled to 22° C.
3. waitThe reaction mixture is aged at room temperature for 24 hours
4. customDuring the age the nicotinate precipitates out of the reaction
5. concentrationThe reaction mixture is concentrated in vacuo
6. customThe crude mixture is chromatographed on silica gel

ORD record

ord-df276dfc5b8f41f39fbda1b70b2c26ca

Source dataset

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05424432