[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:20]([CH2:22][CH2:23][C:24](Cl)=O)#[N:21].O.[NH2:28][NH2:29]>C1(C)C=CC=CC=1.CCO.CC(O)=O>[C:4]1([C:1]2[CH:2]=[C:24]([CH2:23][CH2:22][C:20]#[N:21])[NH:29][N:28]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
To a solution of acetophenone (5.0 g, 41.6 mmol) in dry toluene (10 mL) was added LiHMDS (1.0 M in toluene) via syringe at 0° C. under argon. The reaction was allowed to stir at that temperature for 5 min and 3-cyanopropanoyl chloride (4.89 g, 41.6 mmol) was added via syringe in one portion. The ice bath was removed and AcOH (glacial, 5 mL), EtOH (100 mL), and hydrazine hydrate (6.25 g, 125 mmol) were added. The mixture was brought to reflux for 16 h. After cooled to room temperature, the reaction was concentrated, extracted with EtOAc, dried over MgSO4, and purified by column chromatography to give the title compound as yellowish oil (2.5 g). LCMS m/z=198.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.87 (t, J=4.42 Hz, 2H), 2.92 (t, J=4.04 Hz, 2H), 6.59 (s, 1H), 725-7.48 (m, 3H); 7.63-7.81 (m, 2H), 13.06 (bs, 1H).
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