[Cl:1][C:2]1[C:7]([CH:8]([CH:11]=O)[C:9]#[N:10])=[CH:6][CH:5]=[CH:4][N:3]=1.O.C(O)(=O)C.C(O)C.[NH2:21][NH2:22]>O1CCOCC1>[Cl:1][C:2]1[C:7]([C:8]2[C:9]([NH2:10])=[N:21][NH:22][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1
In a 150 mL sealed tube, added 2-(2-chloropyridin-3-yl)-3-oxopropanenitrile (2.5 g, 14 mmol), water (2.0 mL, 14 mmol), acetic acid (14 mL, 14 mmol), ethanol (28 mL, 14 mmol), 1,4-dioxane (14 mL), and anhydrous hydrazine (0.40 ml, 14 mmol). The mixture was stirred at 70° C. for 20 minutes. The reaction was cooled to RT and concentrated. The concentrate was extracted into EtOAc, washed 1×NaHCO3, 1×H2O, dried over Mg2SO4, filtered through fritted funnel and concentrated. The crude was purified using reverse phase chromatography. The product was extracted into CH2Cl2) washed 1×NaHCO3, 1×H2O, dried with Na2SO4, filtered through fritted funnel, concentrated to yield 4-(2-chloropyridin-3-yl)-1H-pyrazol-3-amine as tan solid. MS m/z=195 [M+1]+. Calc'd for C8H7ClN4: 194.62.
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