[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]#[N:14])=[C:11]([C:15]([O:17]CC)=[O:16])[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-:20]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]([NH2:14])=[O:20])=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1A 14 g. portion of ethyl 1-(3-bromophenyl)-5-cyano-4-pyrazolecarboxylate was hydrolyzed by stirring under reflux in 200 ml. of ethanol with 6 g. ofpotassium hydroxide for 2 hours. The mixture was then poured over ice, acidified and filtered, and the solids were crystallized from ethanol/water and dried at 168° to obtain 10 g. of the desired product, m.p. 215°-217° dec. The product was identified by NMR analysis in CDCl3 /DMSOd6. δ7.06 (s, 1), carboxamide; 7.30-7.64 (m, 4), aromatic; 8.08 (s, 1), pyrazole; 9.10 (s, 1), carboxamide.
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