Ethanol → [2-Nitro-3-(3-nitro-phenylamino)-phenyl]-acetic acid ethyl ester

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Reaction Steps

[2-Nitro-3-(3-nitro-phenylamino)-phenyl]-acetic acid (0.79 g, 2.5 mmol) is refluxed in EtOH (50 ml) in the presence of 0.5 ml concentrated H2SO4 for 2 hours. It is then concentrated and to the residue is added saturated NaHCO3. The mixture is extracted with ethyl acetate (30 ml×3). The organic layers are combined and dried with Na2SO4 to give the desired compound after concentration: 1H NMR (CDCl3) δ 1.29 (t, 3H, J=7.2 Hz), 3.92 (s, 2H), 4.20 (q, 2H, J=7.2 Hz), 6.89 (d, 1H, J=6.0 Hz), 7.34-7.41 (m, 2H), 7.44-7.52 (m, 2H), 7.92 (d, 1H, J=7.6 Hz), 8.03 (s, 1H), 8.17 (s, 1H); LC-MS: 346.0 (MH+).

Provenance & Evidence