[C:1]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[O:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)#[N:2].[N-:25]=[N+:26]=[N-:27].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C)C=O>[N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[CH2:11][O:10][C:9]1[CH:8]=[C:7]([CH:24]=[CH:23][CH:22]=1)[O:6][CH2:5][CH2:4][CH2:3][C:1]1[NH:27][N:26]=[N:25][N:2]=1A mixture of 4.4 g of 2-[3-(3-cyanopropoxy)phenoxymethyl]quinoline 2.6 g of sodium azide and 2.1 g of ammonium chloride in 35 ml of dry dimethylformamide is heated at 140° C. for 18 hours. The reaction mixture is poured onto ice. A solution of 20 ml of 1N sodium hydroxide is added and the solution is extracted twice with ethyl acetate. Concentrated hydrochloric acid is added to acidify the aqueous portion. This is extracted twice with ethyl acetate, dried and evaporated to give 4.5 g of a tan solid. Recrystallization from ethyl acetate gives 1.5 g of pure product of M.P. 147°-149° C.
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