Ammonium Acetate → HCID 59612107, compound

HRID 889649Notes

Reaction equation

HRID 889649 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5](=O)[CH2:6][C:7](=[O:17])/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[CH3:2].C([O-])(=O)C.[NH4+:24]>CCO>[CH2:1]([O:3][C:4](=[O:19])/[C:5](/[NH2:24])=[CH:6]/[C:7](=[O:17])/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[CH3:2]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 53758255-Hexenoic acid, 6-[p-chlorophenyl]-2,4-dioxo-, ethyl ester

Product 1

HCID 59612107HCID 59612107, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Sources & evidence

ORD record
ord-15e48261282d435887b503dba8e9adc6
Source dataset
uspto-grants-2012_08
Patent number
US08252938B2

Reaction notes

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