Benzoic Acid → 3-Nitro-5-sulfobenzoic acid

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Benzoic acid was sulfonated by heating it with concentrated sulfuric acid in the presence of sulfur trioxide. The 3-sulfobenzoic acid was nitrated with fuming nitric acid to yield 3-nitro-5-sulfobenzoic acid. Hydrogenation of this in 50% ethanol/water over palladium on charcoal easily afforded 3-amino-5-sulfobenzoic acid in good yield. Structural verification was obtained by carbon magnetic resonance, proton magnetic resonance and infra-red analysis.

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