Reacción #1994301

Ecuación de reacción

(E)-6-(4-chlorophenyl)-2,4-dioxo-hex-5-enoic acid ethyl ester

(E)-6-(4-Chlorophenyl)-2,4-dioxo-hex-5-enoic acid ethyl ester

ammonium acetate

→

(2Z,5E)-2-amino-6-(4-chlorophenyl)-4-oxo-hexa-2,5-dienoic acid ethyl ester

Rendimiento 86.0%

(2Z,5E)-2-Amino-6-(4-chlorophenyl)-4-oxo-hexa-2,5-dienoic acid ethyl ester

Rendimiento 86.0%

Disolventes

EtOH

Condiciones de reacción

Procedimiento

Using the procedure of Example 4, (E)-6-(4-chlorophenyl)-2,4-dioxo-hex-5-enoic acid ethyl ester (4; 79.5 g, 0.284 mol) and ammonium acetate (43.78 g, 0.568 mol) were allowed to react in EtOH (795 mL) to provide (2Z,5E)-2-amino-6-(4-chlorophenyl)-4-oxo-hexa-2,5-dienoic acid ethyl ester (8; 47 g, 86%) as a yellow solid: mp 105-107° C.; 1H NMR (400 MHz, CDCl3) δ 9.40 (br s, 1H), 7.52 (d, J=15.9 Hz, 1H), 7.50-7.47 (m, 2H), 7.38-7.32 (m, 2H), 6.78 (d, J=15.9 Hz, 1H), 6.14 (s, 1H), 6.01 (s, 1H), 4.37 (q, J=7.1 Hz, 2H), 1.39 (t, J=7.1 Hz, 3H); HRMS-ESI (m/z): calcd for C14H14ClNO3, 279.067. found, 279.066.

Fuente