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Reduction of 1-bromo-l-nitrocyclohexane (I) was then studied using an excess of zinc and ammonium bromide. In this case the only product isolated was cyclohexylamine hydrobromide (IV).When nitrocyclohexane is reduced under the same conditions cyclohexylamine hydrobromide is also formed. When, however, the reaction is stopped after only one hour, N-cyclohexylhydroxylamine (V) is formed as is reported in the literature.2•3The structure of the hydrobromide was confirmed by treatment with aqueous alkali and preparation of W-cyclohexylbenzamide (VI) from the resulting free amine. EXPERIMENTAL 1-Bromo-1-nitrocyclohexane was prepared in 60% yield according to the procedure of Iffland and Criner.4 *Melting points and boiling points are uncorrected. Analyses by Mr. E. M. Hubbard and associates and by Galbraith Laboratories, Knoxville, Tenn.Zinc reduction of 1-bromo-l-nitrocyclohexane (I), (a) To nitrocyclohexane (II). 1-Bromo-l-nitrocyclohexane (20.8 g., 0.10 mole) was mixed with 250 ml. of methanol and 17.6 g. (0.18 mole) of ammonium bromide, 11.6 g. of 90% zinc dust (0.16 mole) added and heating of the mixture begun. As in Klager's experiment, a white precipitate formed almost immediately with concomitant disappearance of the zinc dust. However, the reaction was not stopped at this point but allowed to reflux for 12 hr. further. At the end of the reaction a white solid was still present. After cooling, this solid was removed by filtration, washed with methanol, dried (Abderhalden), and analyzed.