N([O-])=O.[Na+].N[C:6]1[C:7]([O:17][CH3:18])=[C:8]([O:15][CH3:16])[CH:9]=[C:10]([C:12](=[O:14])[CH3:13])[CH:11]=1.[Cu][C:20]#[N:21].[C-]#N.[K+]>O.Cl.C(Cl)Cl>[C:20]([C:6]1[C:7]([O:17][CH3:18])=[C:8]([O:15][CH3:16])[CH:9]=[C:10]([C:12](=[O:14])[CH3:13])[CH:11]=1)#[N:21]
A solution of 5.2 g of sodium nitrite in 20 ml of water is added dropwise at 0° within 20 minutes to 14.0 g of 5'-amino-3',4'-dimethoxyacetophenone dissolved in 155 ml of 1N hydrochloric acid. After stirring at -2° for 30 minutes the cold diazonium salt solution is added dropwise within 30 minutes at 5°-10° to a solution of 8.7 g of copper(I) cyanide and 5.45 g of potassium cyanide in 60 ml of water. After completion of the addition 200 ml of methylene chloride are added, and the reaction mixture is stirred at 23° for 3 hours and then filtered. The organic phase is separated, washed with water, dried over sodium sulfate and evaporated. The residue is recrystallized from methylene chloride/petroleum ether. There is obtained 5'-cyano-3',4'-dimethoxyacetophenone of m.p. 125°-126°.
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