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With hydrazine; In ethanol; for 2.5h;Heating / reflux;Product distribution / selectivity;
[Reference Example 35] 3-Hydrazino-6-methylpyridazine [Show Image] Hydrazine monohydrate (45 mL) was added to a suspension of 3-chloro-6-methylpyridazine (3.00 g) in ethanol (45 mL), and the resultant mixture was heated to reflux for 2.5 hours. After air cooling, a residue obtained by evaporating the solvent of the reaction solution under reduced pressure was purified by silica gel chromatography (chloroform-methanol-water (a lower layer solvent of 7: 3: 1 (v/v)), to obtain the title compound (2.35 g, 81%) as a solid. 1H-NMR(400MHz, DMSO-d6)delta: 2.39(3H, s), 4.20(2H, br), 6.94(1H, d, J=9.3Hz), 7.18(1H, d, J=9.3Hz), 7.64(1H, br). ESI-MSm/z: 125(M+H)+.
80%
With hydrazine; In ethanol; for 3h;Heating / reflux;
Example 11: 6-Methyl-[l,2,4]triazolo[4,3-b]pyridazine-3-thioI; Step 1: (6-Methyl-pyridazin-3-yl)-hydrazine; [0372J To a suspension of 3-chloro-6-methyl-pyridazine (3 g, 23.3 mmol) in ethanol (45 mL) was added hydrazine hydrate (45 mL) and the resultant mixture was heated to reflux for 3 hrs. Most of the solvent was removed under reduced pressure and the white solid was collected by filtration and washed with ethanol. Upon drying 2.3 g of (6-methyl-pyridazin- 3 -yl) -hydrazine was obtained as a white crystalline solid (80% yield).
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