Hydrochloric Acid → 4-(Acetylamino)-3-Aminobenzoic Acid Hydrochloride

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To a stirred mixture of 107 (1.00 g, 4.46 mmol) and 10% Pd-C (1.0 g) in ethanol (10 mL) and 5% HCl (1.2 mL) was added dropwise hydrazine hydrate (55% hydrazine, 1.0 mL, 17 mmol). The mixture was stirred at room temperature for 1 hour, the catalyst was filtered, and the filtrate was concentrated under reduced pressure. Compound 108 (0.875 g, 100%) was obtained as a white solid residue: mp 220-223° C. (methanol/hexane). A literature reference (Ellis and Jones, 1974) did not report the mp.

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