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7.3.13.1.2 Reduction of Nitro and N-Oxide Groups and Hydroxylamines

DOI: 10.1055/sos-SD-107-00076

Araki, S.; Hirashita, T.Science of Synthesis Knowledge Updates, (20104185.

Treatment of a range of aromatic nitro compounds with indium in aqueous ammonium chloride/ethanol results in selective reduction of the nitro groups to amino groups, whereby ester, nitrile, amide, and halide substituents are unaffected.[‌211‌] Several aromatic and aliphatic amine N-oxides are deoxygenated to the corresponding amines in good to quantitative yields using indium metal in neutral aqueous media. Other functional groups such as alkenes, halides, esters, ethers, nitriles, amides, and sulfones are unaffected under the reaction conditions.[‌212‌,‌213‌] Similarly, hydroxylamines are reduced to the corresponding amines, e.g. 101, by means of indium powder in aqueous media. A catalytic version of the process using 2–5% indium in the presence of other metals (Zn, Al) is also operative (Scheme 121).[‌214‌]

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