Ammonium Acetate → (2Z,5E)-2-Amino-6-(4-chlorophenyl)-4-oxo-hexa-2,5-dienoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4](=O)[CH2:5][C:6](=[O:16])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.C([O-])(=O)C.[NH4+:23]>CO>[CH3:1][O:2][C:3](=[O:18])/[C:4](/[NH2:23])=[CH:5]/[C:6](=[O:16])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1Participants
4
Procedure
Using the procedure of Example 4, (E)-6-(4-chlorophenyl)-2,4-dioxo-hex-5-enoic acid methyl ester (6; 21.3 g, 0.008 mol) and ammonium acetate (12.33 g, 0.16 mol) were allowed to react in MeOH (150 mL) to afford (2Z,5E)-2-amino-6-(4-chlorophenyl)-4-oxo-hexa-2,5-dienoic acid methyl ester (9; 15.7 g, 74%) as a yellow solid: mp 112-113° C.; 1H NMR (400 MHz, CDCl3) δ 9.37 (br s, 1H), 7.64-7.42 (m, 3H), 7.38-7.32 (m, 2H), 6.75 (d, J=15.9 Hz, 1H), 6.14 (s, 1H), 5.99 (br s, 1H), 3.91 (s, 3H); HRMS-ESI (m/z): calcd for C13H12ClNO3, 265.050. found, 265.050.