4-Nitronaphthalic anhydride

It is. significant in that it gives not only amines but also o- and p-amino sulfonic acids, all in one reaction. It is generally carried out with excess sodium bisulfite (4.5-6.0 moles per mole of nitro compound), usually with the addition of enough caustic soda to form the required amount of neutral sulfite. A solvent, such as ethyl alcohol or pyridine, often helps to speed up the reaction, particularly for nitro compounds that are either difficultly soluble or wettable. It is interesting to note that sulfamic acids have also been isolated from this reaction in certain cases. Examples of nitro compounds that may be reduced by the Piria method are p-nitrotoluene, which forms p-toluidine in about 70 per cent yield p-nitrobenzoic acid, which forms 4-amino-3-sulfobenzoic acid and 4-nitronaphthalic anhydride, which forms 4-amino-3-sulfonaphthalic anhydride. 

An alternative method for synthesis of similar bis(ethernaphthalic anhydrides) k the reaction involving 4-nitronaphthalic anhydride instead of 4-bromo-... 

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