[ClH:1].O1CCOCC1.[CH3:8][C:9]1[C:14]([N:15](C(OC(C)(C)C)=O)[NH:16]C(OC(C)(C)C)=O)=[CH:13][CH:12]=[CH:11][N:10]=1>CC(O)C.C(OCC)C>[ClH:1].[NH:15]([C:14]1[C:9]([CH3:8])=[N:10][CH:11]=[CH:12][CH:13]=1)[NH2:16]is Hydrogen chloride in dioxane (5.67 mL, 22.67 mmol) was added to a solution of di-tert-butyl 1-(2-methylpyridin-3-yl)hydrazine-1,2-dicarboxylate (Intermediate V1) (733 mg, 2.27 mmol) in IPA (10 mL). The reaction mixture was heated at reflux for 20 mins. The reaction mixture was allowed to cool and then diluted with diethyl ether (30 mL). The resultant precipitate was collected by filtration and dried in vacuo to afford 3-hydrazinyl-2-methylpyridine hydrochloride (362 mg, 100%). 1H NMR (400 MHz, DMSO) δ 2.66 (3H, s), 7.80-7.83 (1H, m), 7.95-7.97 (1H, m), 8.23-8.25 (1H, m), 9.15 (1H, s), 11.30 (1H, s); no ion in LCMS (1NH missing).
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