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By K Venkataraman (Eds.)

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Res. (India) 17B, 33 (1958). 23 I. NAPHTHOQUINONOID DYES AND PIGMENTS I t is interesting to note t h a t whereas benzoylacetonitrile reacts with (I) in the presence of isoquinoline to yield (XLVII), the reaction when carried out in presence of pyridine does not yield a pyrrocoline derivative, but gives 2-phenyl-3-cyano[2,3-&]naphthofuran-4,9-dione (XLVIII). 3 3 2. Synthesis of 2,3-Phthaloylpyrrocolines by Ring Closure of Ylidene-enol Betaines Methylation of the pyridinium betainę (XX) with dimethyl sulfate yields 3-(2-methoxy-l ,4-naphthoquinonyl)pyridinium methosulfate (XLIX).

D . TIL AK In the above reactions pyridine reacts with ethyl chloroacetate to give the quaternary salt (XLII), which can readily form a reactive nitrogen ylid which reacts with the 2-chloro-l,4-naphthoquinone-3-pyridinium chloride (XIX). The formation of the carbanion (XLIV) is followed by cyclization and subsequent removal of pyridine, a very good leaving group. This method gives exclusively l-carbethoxy-2,3-phthaloylpyrrocoline (XXXVI) as against the method using ethyl acetoacetate, in which both (XXXVI) and l-acetyl-2,3-phthaloylpyrrocoline (XL) are formed.

IV. Miscellaneous Dyes 2-Amino-3-chloro-l,4-naphthoquinone (CXIII) obtained by reacting (I) with aqueous ammonia in boiling ethanol is a useful intermediate for synthesis of a few vat dye systems. A. 1-#-NAPHTHO[2,3-Í2]IMIDAZOLE-4,9-DIONE When 2-acetylamino-3-amino-l,4-naphthoquinone is heated with ethyl orthoformate in sulfuric acid, it undergoes cyclization to yield 2-methyl-l-£r-naphtho[2,3-d]imidazole-4,9-dione(CXIV). 68 68 J. R. E. Hoover and A. R. Day, J. Am. Chem. Soc. 76, 4148 (1954). 46 B.

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