Ethyl Acetate → 2-(6-Chloropyridazin-3-yl)acetonitrile
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[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH2:8]Cl)=[CH:6][CH:7]=1.[C-:10]#[N:11].[K+].C(OCC)(=O)C>CS(C)=O.O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH2:8][C:10]#[N:11])=[CH:6][CH:7]=1[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH2:8]Cl)=[CH:6][CH:7]=1.[C-:10]#[N:11].[K+].C(OCC)(=O)C>CS(C)=O.O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH2:8][C:10]#[N:11])=[CH:6][CH:7]=13-Chloro-6-chloromethyl-pyridazine (1.50 g) dissolved in dimethyl sulfoxide (7.5 mL) was added to a solution of potassium cyanide (0.90 g) in water (1 mL) and dimethyl sulfoxide (7.5 mL) stirred at 80° C. The solution was stirred at this temperature for 30 min and then cooled to room temperature. Water and ethyl acetate were added and the resulting mixture was filtered over Celite. The aqueous phase of the filtrate was separated and extracted twice with ethyl acetate. The extracts and the organic phase of the filtrate were combined and washed with brine and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1) to give the title compound as a solid. Yield: 0.23 g (16% of theory); LC (method 2): tR=0.76 min; Mass spectrum (ESI+): m/z=154/156 (Cl) [M+H]+.
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