[O:1]=[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][O:5][C:4]([C:14]#[N:15])=[CH:3]1.[N-:16]=[N+:17]=[N-:18].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[C:8]1([C:7]2[C:2](=[O:1])[CH:3]=[C:4]([C:14]3[NH:18][N:17]=[N:16][N:15]=3)[O:5][CH:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1A mixture of 4-oxo-5-phenyl-4H-pyran-2-carbonitrile (2.0 g), sodium azide (1.0 g) and ammonium chloride (0.8 g) in dimethylformamide (20 ml) was stirred at room temperature for an hour. Ice (20 g) was added and the clear solution was acidified with 2 N hydrochloric acid (20 ml) giving a pale solid which was recrystallised from ethanol to give the title product (mp 237°-238° C. with decomposition).
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