Diethyl Ether → 3-Hydrazinyl-6-phenylpyridazine

HRID 12444

Reaktionsgleichung

Reaktionsgleichung von HRID 12444
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.O.[NH2:15][NH2:16].CCOCC>C(O)(C)C>[C:8]1([C:5]2[N:4]=[N:3][C:2]([NH:15][NH2:16])=[CH:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 24654Hydrazine hydrate (1:1)HCID 885153-Chloro-6-phenylpyridazine2×

Produkt 1

HCID 64098423-Hydrazinyl-6-phenylpyridazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

As shown in FIG. 7, a mixture of 3-chloro-6-phenylpyridazine (compound 1006, 1 g, 5.3 mmol) and hydrazine monohydrate (0.51 mL, 10.53 mmol) in isopropanol was microwaved at 180° C. for 30 minutes. The reaction was treated with ether, the resulting precipitate filtered and washed with ether to yield 1-(6-phenylpyridazin-3-yl)hydrazine, which can be treated with 2M HCl in ether to give the corresponding hydrochloride salt (compound 1007) in quantitative yield. Compound 1007 (0.050 g, 0.22 mmol) and 2-(4-methoxyphenyl)acetic acid (0.044 g, 0.22 mmol) were heated neat to 100° C. for 10 minutes. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and brine. Purification by preparative reversed-phase HPLC yielded 3-(3,4-dimethoxybenzyl)-6-phenyl-[1,2,4]triazolo[4,3-b]pyridazine (compound 206, 0.0073 g, 0.021 mmol, 10% yield).

Aufarbeitung

  1. customwas microwaved at 180° C. for 30 minutes
  2. filtrationthe resulting precipitate filtered
  3. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-f73031f7960e4bc48e15cd4b6620dfa1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728017B2

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