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Iso coumarins 19. syntheses of 8 hydroxy 3 methyl iso coumarin and racemic mellein from m di nitro benzene and a convenient synthesis of 3 methoxy homo phthalic acid



Iso coumarins 19. syntheses of 8 hydroxy 3 methyl iso coumarin and racemic mellein from m di nitro benzene and a convenient synthesis of 3 methoxy homo phthalic acid



Indian Journal of Chemistry Section B Organic Chemistry Including Medicinal Chemistry 17(5): 430-432



6-Methoxy-2-nitrobenzonitrile is treated with PdC/NH2NH2-2H2O in methanol to give in one step 6-methoxyanthranilamide from which 6-methoxy-2-bromobenzoic acid is obtained in one step with the help of diazotization reaction. Condensation of the bromobenzoic acid with ethyl acetoacetate and also with ethyl malonate furnishes 3-methoxyhomophthalic acid. Methyl ether of the natural isocoumarin (VIII) and its 4-carboxy derivative (IX) are synthesized from VI by the Tirodkar-Usgaonkar isocoumarin synthesis using Ac2O-Py and methyl ether of (.+-.)- mellein is synthesized from 4-acetyl-8-methoxyisochroman-1,3-dione (VII) by hydrolyzing it with aq. NaOH and treating the resulting ketone (XI) with NaBH4. Demethylation reaction on VIII and IX furnishes the natural 8-hydroxy-3-methylisocoumarin [from the fungus Marasmius ramealis].

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