Quinoline catalyzed synthesis of pyridazinone pharmaceutical int

Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system

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544224, 544240, 560 35, C07D23714, C07D23724, C07D23722, C07D23718

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active

042811252

ABSTRACT:
Valuable pyridazinone intermediates to pharmaceutically useful compounds can be prepared in surprisingly high yields by the quinoline catalyzed reaction of the corresponding monohydrazone with an appropriately substituted acetic acid ester. In an especially preferred embodiment, p,p'-dichlorobenzil monohydrazone and methyl acetoacetate are reacted in a xylene solvent in the presence of quinoline to afford 4-acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one, which can then be reacted with ethylene carbonate in the presence of potassium carbonate to afford the antihypertensive agent, 4-acetyl-5,6-bis(p-chlorophenyl)-2-(2'-hydroxyethyl)-2H-pyridazin-3-one.

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