[NH2:1][C:2]1[C:6]([C:7](OCC)=[O:8])=[CH:5][N:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH2:1][C:2]1[C:6]([CH2:7][OH:8])=[CH:5][N:4]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1A solution (70 mL) of ethyl 3-amino-1-phenyl-1H-pyrazole-4-carboxylate (17.2 g) in tetrahydrofuran was added dropwise to a mixture of lithium aluminum hydride (3.39 g) and tetrahydrofuran (130 mL) on an ice bath. The reaction mixture was heated under reflux for 2 hrs. To this reaction mixture was added sodium sulfate decahydrate by small portions with stirring until foams disappeared on an ice bath, and tetrahydrofuran (50 mL) was further added. After further stirring for 2 hrs., the reaction mixture was filtered, and the filtrate was concentrated. Recrystallization of the residue from tetrahydrofuran-hexane gave (3-amino-1-phenyl-1H-pyrazol-4-yl)methanol as pale-yellow crystals (10.02 g, yield 82%). The crystals were recrystallized from ethyl acetate-hexane. melting point: 127-128° C.
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