ChemicalBook CAS DataBase List 3-CHLORO-5-METHOXYPYRIDAZINE

3-CHLORO-5-METHOXYPYRIDAZINE synthesis

7synthesis methods

Product Name:3-CHLORO-5-METHOXYPYRIDAZINE
CAS Number:123696-02-6
Molecular formula:C5H5ClN2O
Molecular Weight:144.56

123696-01-5

123696-02-6

5-Methoxypyridazin-3(2H)-one (250 mg, 1.98 mmol) was used as starting material and suspended in phosphoryl chloride (1.5 mL, 16 mmol). The reaction mixture was stirred at 100 °C for 10 min. After completion of the reaction, the mixture was slowly poured into ice water and the pH was adjusted to alkaline by adding sodium carbonate. Subsequently, the mixture was extracted with ether and the organic phases were combined and dried with anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure. The resulting residue was recrystallized with 1,2-dichloroethane to give 130 mg of 3-chloro-5-methoxypyridazine in 45% yield. The product was analyzed by LC-MS (Method 5): r = 0.85 mm; MS (ESIpos): m/z = 145 [M + H]+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.495 (0.78), 2.499 (1.07), 2.503 (0.84), 3.317 (11.94). 3.944 (16.00), 7.528 (2.28), 7.534 (2.29), 8.988 (2.34), 8.994 (2.34).

124-41-4 Synthesis

124-41-4
726 suppliers
$12.00/25g

1837-55-4 Synthesis

1837-55-4
183 suppliers
$23.00/250mg

123696-02-6
137 suppliers
$17.00/250mg

Yield:-

Reaction Conditions:

in methanol at 90; for 1 h;

Steps:

131.1
Example 131 2-Chloro-N-(1 -hydroxy-cyclohexylmethyl)-5-(5-methoxy-pyridazin-3- yloxy)-benzamide131.1 3-chloro-5-methoxyDyridazineTo a solution of 3,5-dichloropyridazine (300 mg) in MeOH (2 mL) was added a 5.4 M solution of sodium methoxide in MeOH (0.410 mL) and the reaction mixture was stirred for 1 h at 90°C. It was quenched with H₂0 and extracted with EtOAc. The organic phase was washed with a 5% solution of KHS0₄, a sat. solution of NaHC0₃ and brine, dried over MgS0₄ and concentrated in vacuo to give the crude titled compound as an orange solid.¹H NMR ((CD₃)₂SO) δ: 9.01 (d, J = 2.4 Hz, 1 H), 7.55 (d, J = 2.4 Hz, 1 H), 3.96 (s, 3 H)

References:

ACTELION PHARMACEUTICALS LTD;HILPERT, Kurt;HUBLER, Francis;MURPHY, Mark;RENNEBERG, Dorte WO2012/114268, 2012, A1 Location in patent:Page/Page column 119

123696-01-5 Synthesis

123696-01-5
93 suppliers
$60.00/100mg

123696-02-6
137 suppliers
$17.00/250mg

References

63910-43-0 Synthesis