O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]([CH3:24])[CH2:22][C:21]([NH:25][CH:26]=O)=[N:20]2)=[CH:15][CH:14]=1.[OH-].[Na+]>O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH:23]([CH3:24])[CH2:22][C:21]([NH:25][CH3:26])=[N:20]2)=[CH:17][CH:18]=1To a stirred solution of 250 ml. of freshly distilled tetrahydrofuran under nitrogen is added cautiously 3.3 g. of lithium aluminum hydride, then 3.3 g. of N-[1-(p-chlorophenyl)-5-methyl-2-pyrazolin-3-yl]formamide is added and the mixture is refluxed under nitrogen for 4 hours. The reaction mixture is cooled. Then with stirring, 3.3 ml. of water is cautiously added dropwise, followed by 3.3 ml. of 15% aqueous sodium hydroxide solution and 10.0 ml. of water. The mixture is filtered and the residue is washed with ether. The combined filtrate and wash is evaporated to dryness giving a gum which solidifies. The solid is collected, washed with hexane and dried. The product of the Example is recrystallized from dichloromethane-hexane to give 2.3 g. of white crystals, m.p. 102°-103° C.
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