[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:17]=[N+:18]=[N-:19].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[N:17]=[N:18][NH:19][N:14]=2)=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1To a solution of 4-benzyloxybenzonitrile (2.0 g) in dimethylformamide (15 mL) were added sodium azide (932 mg) and ammonium chloride (767 mg). The mixture was stirred at 110° C. overnight under heating and then allowed to stand for cooling to room temperature. 1N aqueous sodium hydroxide was added thereto to adjust the pH to about 10, followed by washing with diethyl ether. To the aqueous layer was added 1N hydrochloric acid, and the resulting precipitated solid was filtered to give the title compound (2.29 g).
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