[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1N)([O-:3])=[O:2].[CH3:11][O:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17][CH:16]=1)=[O:14].[N:24]1C=CC=CC=1>C1COCC1.C(=O)(O)[O-].[Na+].CCOC(C)=O>[CH3:11][O:12][C:13](=[O:14])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH2:24])=[O:22])=[CH:17][C:16]=1[C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2]A solution of 2-nitroaniline (0.41 g, 3.0 mmol) and methyl 4-chlorocarbonyl benzoate (0.65 g, 3.3 mmol) in THF (3.7 mL) and pyridine (0.8 mL) was stirred for 2 h at room temperature. The reaction was diluted with saturated sodium bicarbonate (10 mL) and EtOAc (15 mL), the phases separated and the aqueous phase extracted with EtOAc (2×10 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to afford (2-nitrophenyl)-terephthalamic acid methyl ester as a yellow solid (0.70 g, 78%). 1H NMR (CDCl3) δ 3.97 (s, 3H), 7.25 (t, 1H, J=7.8 Hz), 7.74 (t, 1H, J=7.8 Hz), 8.04 (d, 2H, J=7.8 Hz), 8.20 (s, 1H (NH)), 8.20 (d, 2H, J=7.8 Hz), 8.30 (d, 1H, J=7.8 Hz), 8.99 (d, 1H, J=7.8 Hz).
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