[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Li+]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][NH2:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1
A solution of 1H-indazole-5-carbonitrile (100 mg, 0.699 mmol) in tetrahydrofuran (4 ml) was added to a solution of lithium aluminum hydride (53 mg, 1.40 mmol) in tetrahydrofuran (4 ml) at room temperature, and the resulting mixture was refluxed for 2 hours. Subsequently, water (0.053 ml), a 2N-aqueous lithium hydroxide solution (0.106 ml) and water (0.212 ml) were added in that order to the reaction solution and stirred, followed by filtration. The solvent was distilled off under reduced pressure and the residue was dried under reduced pressure to obtain 1-(1H-indazol-5-yl)methanamine (97 mg, 94%).
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