4,5-Dihydro-6-(4-methoxyphenyl)pyridazin-3(2H)-one synthesis

7synthesis methods

Product Name:4,5-Dihydro-6-(4-methoxyphenyl)pyridazin-3(2H)-one
CAS Number:1017-06-7
Molecular formula:C11H12N2O2
Molecular Weight:204.23

3153-44-4
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4,5-Dihydro-6-(4-methoxyphenyl)pyridazin-3(2H)-one

1017-06-7
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Yield:1017-06-7 98%

Reaction Conditions:

with carbazic acid at 90; for 3 h;Green chemistry;

Steps:

3. General procedure for the solid state or solvent-free reactions between 1a and di-carbonyl compounds.

General procedure: A 10.0 mmol for α-keto acid compound or a 5.2 mmol for β-diketones or α-keto acids was mixed with 0.40 g of hydrazinium carboxylate (1a, 5.2 mmol), respectively. (For solid di-carbonyl compound, the mixture was ground using a pestle and a mortar.) The mixture was stored in a closed vial, and then heated to 70 - 90 °C until the reaction was complete. Complete conversion to related product was dependent upon the nature of di-carbonyl compounds. Typically, those di-carbonyl compounds take about <3 h to complete the reactions. CO2 and water were released during the reaction. All products obtained from the reactions of 1a with di-carbonyl compounds were basically characterized by 1H and 13C NMR spectroscopy. The products have over 97% of purity of reaction mixture based on 1H NMR spectroscopy and isolation yields are over 97% based on di-carbonyl compounds. The melting points, elemental analysis and UV-Vis spectra for all azines, pyrazoles and pyridazinones, were measured after purification using appropriate solvent.

References:

Lee, Byeongno;Kang, Philjun;Lee, Kyu Hyung;Cho, Jaeheung;Nam, Wonwoo;Lee, Won Koo;Hur, Nam Hwi [Tetrahedron Letters,2013,vol. 54,# 11,p. 1384 - 1388] Location in patent:supporting information