Acetic Acid → 5-Bromo-2-(tetrahydropyran-4-yl)aminoaniline

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Reaction Steps

A 3-neck flask was charged with 5-bromo-2-(tetrahydropyran-4-yl)nitrobenzene (see Working Example 18-1) (3.54 g, 11.8 mmol) and 10% aqueous acetic acid solution (65 mL), after which electrolytic iron (6.56 g, 118 mmol) was added and this was refluxed with stirring for 15 minutes. After this was allowed to cool to room temperature, the insoluble material was filtered off through Celite, and this same layer was further washed with 10% aqueous acetic acid solution (65 mL). The filtrate and the wash solutions were combined and then successively extracted with ethyl acetate (approx. 50 mL, 4 times), washed with distilled water (30 mL), and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and further drying under reduced pressure yielded the title compound (2.72 g, 85.4% yield) as a pale yellow solid.

Provenance & Evidence