Ammonium Acetate → (2Z,5E)-2-Amino-6-(4-chlorophenyl)-4-oxo-hexa-2,5-dienoic acid methyl ester

HRID 889650Notes

Reaction equation

HRID 889650 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]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 59612126(E)-6-(4-chlorophenyl)-2,4-dioxo-hex-5-enoic acid methyl ester

Product 1

HCID 59612131(2Z,5E)-2-Amino-6-(4-chlorophenyl)-4-oxo-hexa-2,5-dienoic acid methyl esterYield 738.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Sources & evidence

ORD record
ord-15bf0c29a5504019b59eeed4114a0a7b
Source dataset
uspto-grants-2012_08
Patent number
US08252938B2

Reaction notes

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