Hydrochloric Acid → diethyl 4-aminobenzene-1,2-dicarboxylate

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Reaction Steps

Compound 401 (1.5 g, 5.6 mmol) was dissolved in 280 ml of benzene, and 3.4 g of purified zinc dust was added. Then 10 ml of concentrated hydrochloric acid was added in portions. After 15 min. of stirring at room temperature, another 3.4 g of zinc dust was added and the mixture was stirred at room temperature for 12 hours. 340 ml of cold water was added to the reaction mixture and the mixture was neutralized with 1N NaOH solution. The mixture was transferred to a separatory funnel and the benzene layer was removed. The aqueous layer was extracted with benzene. The combined benzene extracts were washed with water and dried over anhydrous sodium sulfate. After evaporation of the solvent, the pale yellow crude solid was obtained and purified by silica gel column chromatography (n-hexane: acetic acid =8:1) to give 1.1 g (80.6%) of diethyl 4-aminophthalate (compound 402).

Provenance & Evidence