반응 #49977

반응 방정식

2,4-pentanedione

ethyl 3-amino-3-ethoxyacrylate hydrochloride

4-methoxybenzylamine

ethyl 2-(4-methoxybenzylamino )-4,6-dimethylnicotinate

potassium hydroxide

→

product

수율 70.0%

2-(4-methoxybenzylamino)-4,6-dimethylnicotinamide

수율 70.0%

용매

ethanol

반응 조건

후처리

1. 1
   온도The reaction mixture was heated to 80° C. for 3 h
2. 2
   온도The reaction is cooled to 22° C.
3. 3
   workup.WAITThe reaction mixture is aged at room temperature for 24 hours
4. 4
   기타During the age the nicotinate precipitates out of the reaction
5. 5
   농축The reaction mixture is concentrated in vacuo
6. 6
   기타The crude mixture is chromatographed on silica gel

실험 절차

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.

출처