[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO.[Cl-].[NH4+]>O1CCCC1.O>[O:7]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][NH2:21])[CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1Next, to a solution of lithium aluminum hydride (725 mg, 19.1 mmol) in tetrahydrofuran (6.0 mL) was portionwise added a solution of the resulting 4-phenoxy-pyridine-2-carbonitrile (1.5 g, 7.65 mmol) in tetrahydrofuran (3 mL) on an ice bath, and the solution was stirred at room temperature for 15 hours. A mixture solvent of methanol and water (9:1) was added to the reaction solution, an aqueous solution of saturated ammonium chloride was further added, the solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, then, the solvent was evaporated to obtain the title compound (730 mg, 48%) as a pale brown oil. This was used in the next reaction without further purification.
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