Reacción #69102

Ecuación de reacción

diphenyl ether

ethyl 4-(4-aminophenoxy)butanoate

hydrochloric acid

→

solid

Rendimiento 42.0%

6-(3-Ethoxycarbonylpropoxy)-2-methylquinolin-4-ol

Rendimiento 42.0%

Condiciones de reacción

Procedimiento

To a stirring mixture of ethyl 4-(4-aminophenoxy)butanoate (3.12 g, 14 mmol) and acetoacetic ester (1.82 g, 14 mmol) was added a catalytic amount of hydrochloric acid and cyclized in refluxing diphenyl ether as described in Example 5a. The product was obtained as a light yellow solid (1.70 g, 42%). 1H NMR (400 MHz, DMSO-d6): 1.32 (3H, t, J=7.1 Hz), 2.15 (2H, m), 2.50 (3H, s), 2.62 (2H, t, J=7.3 Hz), 4.21 (4H, m), 6.09 (1H, s), 7.42 (1H, dd, J=9.0, 2.7 Hz), 7.58 (1H, d, J=2.7 Hz), 7.65 (1H, d, J=9.0 Hz), 11.8 (1H, s).

Fuente