N[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:13](Cl)(=[O:18])[CH2:14][CH2:15][CH:16]=[CH2:17].C([N:23](C(C)C)CC)(C)C.O>C1COCC1>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([NH:23][C:13](=[O:18])[CH2:14][CH2:15][CH:16]=[CH2:17])=[C:9]([N+:10]([O-:12])=[O:11])[CH:2]=1)#[N:5]To a solution of 2-amino-3-nitrobenzonitrile (2 g) in THF (30 ml) were added 4-pentenoyl chloride (2.90 g) and diisopropylethylamine (4.27 ml), followed by stirring at 80° C. for 12 hours. The reaction solution was poured into water, and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:CH3OH) to obtain N-(4-cyano-2-nitrophenyl)pent-4-enamide (174 mg) as a colorless liquid.
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