I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:11][C:12]1[N:16]([CH3:17])[N:15]=[C:14]([CH3:18])[CH:13]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C>[CH3:17][N:16]1[C:12]([NH:11][C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:13][C:14]([CH3:18])=[N:15]1
A mixture of 2-iodobenzoic acid (14.9 g, 0.06 mol), 5-amino-1,3-dimethylpyrazole (6.7 g, 0.06 mol), DMF (125 ml), Cu(OAc)2 (0,4 g) and K2CO3 (8.28 g, 0.06 mol) was refluxed overnight. The reaction mixture was poured into ice-water (500 ml) and then was acidified with acetic acid to a pH of about 5. The solid which formed was collected by filtration, washed with water (100 ml) and dried. The solid was dissolved in hot CHCl3 (300 ml), filtered, dried over MgSO4 and evaporated to about 20 ml. Hexane (50 ml) was added and then the product was collected by filtration, washed with hexane (30 ml) and dried to afford 6.2 g of N-(1,3-dimethyl-pyrazol-5-yl)anthranilic acid, m.p. 210-211° C.
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