Tetrachlorophthalic anhydride → 4,8-Dimethyl-6-(3,4,5,6-tetrachlorophthalimido)-quinaldine

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Reaction Steps

350 g of o-dichlorobenzene was added to 186 g (1.0 mole) of 6-amino-4,8-dimethylquinaldine and 286 g (1.0 mole) of 3,4,5,6-tetrachlorophthalic anhydride, and the mixture was refluxed at the boiling point for 4 hours. The reaction mixture was then cooled. The crystals precipitated were collected by filtration, and dried to afford 394 g (0.87 mole) of 4,8-dimethyl-6-(3,4,5,6-tetrachlorophthalimido)-quinaldine. Then, 372 g (1.30 moles) of 3,4,5,6-tetrachlorophthalic anhydride, 2,000 g of 1,2,4-trichlorobenzene and 40 g of anhydrous zinc chloride were added, and the mixture was heated under reflux for 3 hours. Then, 500 g of dimethylformamide was added, and the mixture was stirred under reflux for 1 hour. The product was treated in the same way as in paragraph (C) of Example 1 to afford 571 g (0.79 mole) of a yellow compound. Since the compound obtained was scarcely soluble in dimethylformamide, its visible spectrum could not be measured. In its infrared spectrum (KBr), absorptions ascribable to --CO--N--CO-- were observed at 1730 cm-1 and 1790 cm-1, and absorptions ascribable to --CO--C--CO--, at 1645 cm-1 and 1695 cm-1. The elemental analysis values of this product were as follows:

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