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not previously been found to result directly from the reduction of a nitro compound.The work of Paul5 has demonstrated that aliphatic aldoximes in contact with Raney nickel will spontaneously rearrange upon gentle heating to the corresponding amides. It is therefore likely that some of the intermediate oxime (un-isolated) rearranged in the course of the present reductionIt is possible that the reduction of a nitro compound or an oxime to an amine proceeds by way of the intermediate amide. However, the difficulty of reducing amides to amines6 7would indicate that this is probably not the most important reaction.Experimental Reduction of Dinitroneopentane.-A solution of 97.2 g. (0.6 mole) of dinitroneopentane in 750 ml. of absolute alcohol was placed in a hydrogenation bomb with 6 g. of Raney nickel catalyst. The hydrogenation proceeded at 1000 p. s. i. and 60°, requiring about two hours for completion. The contents of the bomb were placed in a beaker and allowed to stand at room temperature for twentyfour hours. The crystalline material and the catalyst were then filtered, and the crystalline material was removed from the mixture of extraction with hot water. Cooling the hot water solution gave white crystals, m. p. 268-269°, after one recrystallization from water. A second crop of the above compound was obtained by partly evaporating the alcohol from the original reaction mixture.

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