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28657-80-9

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Method for the production of 1-alkyl-6,7-methylene-dioxy-4(1H)-oxo-cinnolin-3-carboxylic acids
A method is disclosed for production of 1-alkyl-4(1H)-oxo-cinnolin-3-carboxylic acids. Mesoxalic acid dialkylester-3,4-methylenedioxy-phenylhydrazone is saponified using 1 to 1.5 Mol alkali into the corresponding monoalkylester, which is cyclicized with a Friedel-Crafts catalyst in the presence of a carboxylic acid anhydride into 6,7-methylenedioxy-4(1H)-oxo-cinnolin-3-carboxylic acid alkylester, which is alkylated with a C1 -C4 alkyl halogenide in the presence of alkali in a suitable solvent, after which the ester is saponified. Small amounts of byproduct alkylated in the 2-position are removed by brief heating and precipitation from alkaline solution, leaving a pure 1-alkyl product. The product is useful for the treatment of urinary tract infections.
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(2008/06/13)

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Chemical Properties

Melting Point: 261-262° (dec)
Boiling Point: 517.2°Cat760mmHg
Flash Point:266.6°C
Density: 1.64g/cm³
Solubility:1 M NaOH: soluble50mg/mL
Storage Temp.:2-8°C
Vapor Pressure: 1.61E-11mmHg at 25°C
Refractive Index: 1.6660 (estimate)
PKA: pKa 5.38(H2O t=25.0 I=0.025) (Uncertain)
PSA: 90.65000
LogP: 0.84330

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