Acetic Acid → 2-(2-(4-Methoxycarbonylphenylmethyl)aminoanilin-5-yl)benzoxazole

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Reaction Steps

To 2-(2-(4-methoxycarbonylphenylmethyl)aminonitrobenzen-5-yl)benzoxazole (see Working Example 113-2) (367 mg, 0.910 mmol) was added iron powder (102 mg, 1.82 mmol), 10% aqueous acetic acid (5 mL) and methanol (7 mL), and this was heated to reflux for 16 hours. After the reaction solution was cooled, saturated aqueous sodium hydrogen carbonate solution and chloroform were added, this was filtered through Celite, and the filtrate obtained was extracted. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (61.8 mg, 18% yield).

Provenance & Evidence