[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:34](O)(=[O:37])[CH:35]=[CH2:36]>C(Cl)Cl.CCOC(C)=O>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:34](=[O:37])[CH:35]=[CH2:36])=[CH:6][CH:5]=1)([O-:3])=[O:2]
4-Nitroaniline (0.4 g, 2.9 mmol) was dissolved in CH2Cl2 (15 ml). To this solution was added EDC (1.67 g, 8.7 mmol), HOBT (1.17 g, 8.7 mmol), DIEA (2.5 ml, 14.5 mmol) and acrylic acid (0.79 ml, 11.6 mmol). The reaction mixture was kept at RT for 4.5 h. The reaction mixture was diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO41 filtered, and evaporated in vacuo. The residue was purified by column chromatography using 2:1 EtOAc/hexanes as the solvent to give N-(4-nitrophenyl)-acrylamide.
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