ChemicalBook CAS DataBase List Pyridazin-3-amine

Pyridazin-3-amine synthesis

5synthesis methods

Product Name:Pyridazin-3-amine
CAS Number:5469-70-5
Molecular formula:C4H5N3
Molecular Weight:95.1

5469-69-2

5469-70-5

General procedure for the synthesis of pyridazin-3-amine from 3-amino-6-chloropyridazine: (1) 6-chloropyridazin-3-amine (5.00 g, 38.6 mmol), tetrahydrofuran (240 mL), sodium hydroxide (8.00 g, 200 mmol), water (32 mL), and 10% palladium-carbon catalyst (500 mg) were mixed, and the reaction was stirred at room temperature in a hydrogen atmosphere for 2 days. After completion of the reaction, the insoluble material was removed by filtration and the filtrate was concentrated. The residue was dissolved in methanol (100 mL), filtered again to remove insoluble matter, and the filtrate was concentrated to quantitatively obtain the target product pyridazin-3-amine as a solid. 1H-NMR (DMSO-d6) δ: 2.51 (2H, broad peak), 6.46-6.49 (1H, multiple peaks), 6.93-6.97 (1H, multiple peaks), 8.06-8.08 (1H, multiple peaks).

5469-69-2 Synthesis

5469-69-2
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5469-70-5
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Yield:5469-70-5 100%

Reaction Conditions:

with sodium hydroxide;hydrogen;palladium 10% on activated carbon in tetrahydrofuran;water at 20; for 48 h;

Steps:

147.1
Example 147; 4-(3-Phenyl-1,2,4-thiadiazol-5-yl)-N-pyridazine-1-carboxamide; (1) Pyridazine-3-amine; A mixture of 6-chloropyridazine-3-amine (5.00 g, 38.6 mmol), tetrahydrofuran (240 ml), sodium hydroxide (8.00 g, 200 mmol), water (32 ml) and 10% palladium-carbon (500 mg) was stirred under a hydrogen atmosphere at room temperature for 2 days, insolubles were filtered off and the filtrate was concentrated. The residue was dissolved in methanol (100 ml), insolubles were filtered off and the filtrate was concentrated to obtain the desired product as a solid quantitatively. ¹H-NMR (DMSO-d₆) δ; 2.51 (2H, br s), 6.46 - 6.49 (1H, m), 6.93 - 6.97 (1H, m), 8.06 - 8.08 (1H, m).

References:

Takeda Pharmaceutical Company Limited EP1813606, 2007, A1 Location in patent:Page/Page column 82

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1120-95-2 Synthesis