[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])(=O)C.[NH4+].C(O)(=O)C.[C:22](#[N:26])[CH2:23][C:24]#[N:25]>O1CCOCC1.C1(C)C=CC=CC=1.[Cl-].[Na+].O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[C:23]([C:22]#[N:26])[C:24]#[N:25])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]p-Nitro-acetophenone (165 g/mole; 4.0 g; 24 mmoles), ammonium acetate (0.50 g) and glacial acetic acid (0.80 mL) were added to a round-bottom flask containing 20 mL toluene, and heated to reflux using a Dean-Stark trap and a reflux condenser. Separately, malononitrile (66 g/mole; 2.0 g; 30.3 mmoles) was dissolved in 5 mL dioxane and 20 mL toluene, transferred to an addition funnel and added dropwise to the heated solution of ketone. Upon completion of the addition, the system was heated for 2 hours and then cooled to room temperature. The reaction mixture was poured into 150 mL brine and 100 mL ethyl acetate. The aqueous layer was separated and washed with 50 mL ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the crude product 2-[1-(4-nitrophenyl)-ethylidene]-malononitrile (213 g/mole) was used as such in Intermediate Example 11.
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