[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1.O(CC)P(OP(OCC)OCC)OCC>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1)=[O:9]A mixture of 5-Chlorosalicylic acid (0.338 g, 1.9 mmol), m-Toluidine (0.2 g, 1.9 mmol) and Tetraethyl pyrophosphite (0.53 g, 2.0 mmol) in dry toluene was refluxed 7 hrs under nitrogen atmosphere. It was diluted with ethyl acetate, washed with HCl (10%) and then with water (3×30 mL). The organic layer was dried (Na2SO4), filtered and evaporated under vacuum. The resulting crude material was purified by column chromatography over SiO2 using mixture of ethyl acetate and hexanes (2:8) to give title compound (0.134 g,) 1H NMR (CDCl3/DMSO-d6) δ 2.38 (s, 3H), 6.89-7.03 (m, 2H), 7.19-7.59 (m, 4H), 8.08 (d, 1H), 9.92 (bs, 1H), 12.05 (s, 1H).
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