I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:11]([N:13]1[C:17]([NH2:18])=[CH:16][C:15]([CH3:19])=[N:14]1)[CH3:12].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].O.C(O)(=O)C>[CH2:11]([N:13]1[C:17]([NH:18][C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:16][C:15]([CH3:19])=[N:14]1)[CH3:12]A mixture of 2-iodobenzoic acid (14.88 g, 0.06 mol), 1-ethyl-3-methyl-5-aminopyrazole (7.5 g, 0.06 mol), DMF (50 ml), Cu(OAc)2.H2O (0.5 g) and potassium carbonate (8.3 g, 0.06 mol) was refluxed for 20 hours. The reaction mixture was cooled to room temperature, poured into ice-water and neutralized with acetic acid. A solid formed which was collected by filtration, washed with water and dried to give 7.1 g (98%) of N- (1-ethyl-3-methylpyrazol-5-yl) anthranilic acid.
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