[Cl-].[C:2]([CH2:5][N+]1C=CC=CC=1)(=[O:4])[NH2:3].[CH:12]([C:14](=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])[C:15]#[N:16])=O.C(N(CC)CC)C.[Cl-].ClC=[N+](C)C>CO>[OH:4][C:2]1[CH:5]=[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[C:14]([C:15]#[N:16])=[CH:12][N:3]=11.726 g (10.0 mmol) 1-carbamoylmethyl-pyridinium chloride and 1.712 g (10.0 mmol) 2-formyl-3-o-tolyl-acrylonitrile in 24.8 ml methanol were treated with 1.05 g (10.4 mmol) triethylamine at 20-30° C. The reaction mixture was stirred for 2 hours and concentrated in vacuo (rotary evaporator at 40° C. and 20 mbar). The residue was taken up in 50 ml dichloromethane, treated with 2.56 g (20.0 mmol) (chloromethylene)dimethylammonium chloride (Vilsmeiers Reagent) and heated at 45° C. for 1 hour. In order to remove all volatile matter, the mixture was concentrated in vacuo (rotary evaporator at 45° C. and 20 mbar). The residue was heated to 180-190° C. for 15 minutes, cooled down to 20-25° C. and distributed in 80.0 ml dichloromethane and 80.0 ml water. The layers were separated. Evaporation of the organic phase in vacuo gave 1.37 g of amorphous product of 6-hydroxy-4-o-tolyl-nicotinonitrile.
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