Cl[C:2](=[CH2:5])[C:3]#[N:4].Cl.[CH:7]([NH:10][NH2:11])([CH3:9])[CH3:8].C(=O)([O-])[O-].[K+].[K+]>O>[CH:7]([N:10]1[CH:5]=[CH:2][C:3]([NH2:4])=[N:11]1)([CH3:9])[CH3:8]2-Chloroacrylonitrile (3.41 mL, 42.59 mmol) was added at RT to a stirring solution of N-isopropylhydrazine hydrochloride (4.71 g, 42.6 mmol), potassium carbonate (11.8 g, 85.2 mmol) in water (50 mL). The reaction was warmed to 45° C. for 4 hours before cooling back to RT. The aqueous layer was then extracted with ethyl acetate (5×30 mL) and the combined organic layers were dried (MgSO4), treated with activated charcoal, filtered and evaporated. The residue was purified by chromatography, eluting with 67%-100% ethyl acetate in hexanes, to afford the title compound (3.08 g, 58%) as a 6:1 mixture of authentic product to regioisomeric product as an oil. The material was used without further purification.
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