ChemicalBook CAS DataBase List 4-AMINO-6-PHENYL-3(2H)-PYRIDAZINONE

4-AMINO-6-PHENYL-3(2H)-PYRIDAZINONE synthesis

6synthesis methods

Product Name:4-AMINO-6-PHENYL-3(2H)-PYRIDAZINONE
CAS Number:89868-06-4
Molecular formula:C10H9N3O
Molecular Weight:187.2

2166-31-6 Synthesis

2166-31-6
130 suppliers
$16.00/250mg

89868-06-4
18 suppliers
$334.75/250mg

Yield:89868-06-4 60.7%

Reaction Conditions:

with hydrazine hydrate at 120;Inert atmosphere;

Steps:

104.104A Example 104A
4-amino-6-phenylpyridazin-3(2H)-one

Example 104A
4-amino-6-phenylpyridazin-3(2H)-one
A mixture of 6-phenylpyridazin-3(2H)-one (1 g, 5.81 mmol) and hydrazine monohydrate (15 mL, 309 mmol) was heated at 120° C. under N₂ for 90 minutes.
Mixture was cooled and more hydrazine monohydrate (15 mL, 309 mmol) was added.
The mixture was heated at 120° C. over night.
The mixture was cooled and the resulting solid was collected by filtration and washed with water.
The solid was taken up in acetonitrile (20 mL) and stirred for 5 minutes.
The solid was collected by filtration, washed with acetonitrile and dried under vacuum to provide the title compound (0.66 g, 3.53 mmol, 60.7% yield).
¹H NMR (400 MHz, DMSO-d₆) δ ppm 12.66 (bs, 1H), 7.75-7.70 (m, 2H), 7.47-7.36 (m, 3H), 6.74 (s, 1H), 6.43 (bs, 2H); MS (ESI+) m/z 188 (M+H)⁺.

References:

US2017/15675,2017,A1 Location in patent:Paragraph 1188