Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[CH3:10][O:11][CH2:12][CH2:13][O-:14].[Na+].[NH2:16][NH2:17]>COCCO>[NH:16]([C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:14][CH2:13][CH2:12][O:11][CH3:10])=[CH:4][N:3]=1)[NH2:17]To a solution of 2-chloro-5-(chloromethyl)pyridine (1620 mg, 10 mmol) in 2-methoxyethanol (10 mL) was added sodium 2-methoxyethanolate (5.9 g, 12.00 mmol). The mixture was stirred at room temperature for 10 min and then at 50° C. for 2 hrs. Hydrazine (1.6 g, 50.0 mmol) was then added to the mixture and the reaction was heated at 120° C. for 1 hr. The mixture was purified by preparative LCMS to provide the title compound, 2-hydrazinyl-5-((2-methoxyethoxy)methyl)pyridine (540 mg, 27.4% yield).
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