N#N.[CH3:3]/[C:4](=[CH:8]\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)/[C:5](O)=[O:6].CC[N:17](CC)CC.ClC(OCC)=O.[NH4+].[OH-]>C1COCC1>[CH3:3]/[C:4](=[CH:8]\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)/[C:5]([NH2:17])=[O:6]
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (E)-2-methyl-3-phenylacrylic acid (19.0 g, 116 mmol) and Et3N (17.1 mL, 122 mmol) in THF (500 mL) at 0° C. was treated with ethyl chloroformate (11.4 mL, 117 mmol) and the reaction mixture was stirred at 0° C. for 15 min. A solution of NH4OH (250 mL of a 25% aq. solution) in THF (150 mL) was then added and the reaction mixture was stirred at rt for 90 min. The aq. layer was extracted twice with CH2Cl2 and the combined org. extracts were washed with water, dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a white solid. TLC:rf (1000:50:4 CH2Cl2—MeOH—NH4OH)=0.25
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