4,5-Dichloro-2-methyl-3(2H)-pyridazinone

Off-white to yellow low crystalline powder

4-Chloro-5-(3-cyclobutyl-2, 3, 4, 5-tetrahydro-lH-benzo[d]azepin-7-yloxy)-2-methyl-2H- pyridazin-3-one; General synthesis of Step 1.; To a round-bottom flask was added 4, 5-dichloro-2H-pyridazin-3-one (10.0 g, 60.6 mmol), potassium carbonate (16.8 g, 121.2 mmol), iodomethane (4.0 mL, 64.3 mmol), and 25 g (151 mmoles) of 4, 5-dichloropyridazinone are placed in a stainless steel reactor in the presence of 25.13 g (181 mmoles) K4.5- dichloro-2-methyl-pyridazin-3-one To a stirred solution of 4, 5-dichloro-lH-pyridazin-6-one (25.0 g, 152 mmol) in N, N-dimethylformamide (152 ml) was added potassium carbonate (25.4 g, 182 mmol) and iodomethane (25.8 g, 182 mmol, 11.3 ml). The resulting mixture was stirred at room temperature overnight. The reaction mixture was then poured onto ice-water (300ml) and the mixture stirred for 15 mins. The resulting precipitate was collected by filtration, then dissolved in dichloromethane and passed through a phase separation cartridge. The organics were concentrated in vacuo to give 19.7 g of a pale brown solid. 1H NMR (400 MHz, Chloroform) d ppm 3.83 (s, 3 H) 7.77 (s, 1 H)The starting material 4, 5-Dichloro-2-phenyl-3(2H) pyridazinone (1a) was purchased from Aldrich. 4, 5-Dichloro-2-(4-trifluoromethyl)phenyl-3(2H)pyridazinone (1b); 4, 5-Dichloro-2-methyl-3(2H)pyridazinone (1c) were prepared by reactions of mucochloric acid with the respective hydrazine in dilute hydrochloric acid.General procedure: Cooling of mucochloric acid (0 ° C.) solution was treated in one portion with sodium carbonate, until complete melting and stirring by observation. Then, the resulting mixture was treated with a substituted hydrazine and stirred for 2.5 to 5 hours while slowly warming to ambient temperature. Furthermore, the newly formed by construction, water is completely clean, funnel and partially dried, and then, dissolved in acetic acid, heated under reflux. 30 after minutes, cooled to ambient temperature a solution, removing all of the volatile matter in reduced pressure. Subsequently, coarse phenylpyridazinone dissolved in a suitable organic solvent, aqueous base by washing, drying, filtering, concd. under decompression. The coarse material is obtained in this way, typically, additional purification is performed using, instead, can be further refined by silica chromatography. According to a general method A, mucochloric acid (2. 03g, 12. 1mmol), sodium carbonate (0. 640g, 6. 03mmol) and methyl hydrazine (0. 555g, 12. 1mmol) is prepared. Isolation yield -0. 840g; 38. 8percent.

Molecular Weight:179.00
XLogP3:1.1
Hydrogen Bond Acceptor Count:2
Exact Mass:177.9700681
Monoisotopic Mass:177.9700681
Topological Polar Surface Area:32.7
Heavy Atom Count:10
Complexity:234
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes