Naphthyridinium-4-olates

Photolysis of the lutidine (V-imide 260 gives a crystalline compound, mp 226-228 C, which appears to be betaine 259 (R = Ph, = Me) (15%). (See also Section III,B, 16.) 

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Alkylation of 4-hydroxy-l,7-naphthyridines gives 4-hydroxy-l,7-naph-thyridinium iodides (254) which on treatment with aqueous alkali yield l,7-naphthyridinium-4-olates (253). A number of derivatives (253 R = H, CN, CO2H) have been prepared in this manner. On the basis of IR spectroscopy, the acid derivatives (253 R = CO2H) have been formulated as mesomeric betaines rather than the inner salts 255. 

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