REDUCTIONS WITH HYDRAZINE HYDRATE CATALYZED BY RANEY NICKEL .2. AROMATIC NITRO COMPOUNDS TO INTERMEDIATE PRODUCTS
REDUCTIONS WITH HYDRAZINE HYDRATE CATALYZED BY RANEY NICKEL .2. AROMATIC NITRO COMPOUNDS TO INTERMEDIATE PRODUCTS
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DOI：
10.1021/ja01577a044
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发表时间：
1957-01-01
影响因子：
15
通讯作者：
MOORE, RE
中科院分区：
文献类型：
--
作者：
FURST, A;MOORE, RE
在Raney镍的存在下，水合肼可以很好地将芳香硝基化合物的醇溶液还原为相应的胺。该方法已成功地应用于将6-硝基吲哚还原为6-氨基吲哚和将一种硝基环秋水仙碱酯转化为相应的胺。将该方法应用于硝基-6或亚硝基吡啶，得到了不易表征的异常产物。很明显，催化剂的性质对反应的进行并不重要。以钯化炭8·9或铂10为催化剂，得到了均匀良好的胺收率。也曾使用过铁粉或铜粉，但产率较差。催化作用可能仅仅是提供还原的表面，因为还原产物仅使用多孔瓦作为催化剂获得。然而，在室温或蒸汽浴温度下，没有催化剂就不会发生还原。3·10·13联氨浓度是控制还原产物性质和产率的主要因素。如果使用大量的酒精，因此使用低浓度的水合肼，则胺是唯一的产物。提高水合肼浓度，中间产物收率较高；的
Hydrazine hydrate in the presence of Raney nickel has been found to reduce alcoholic solutions of aromatic nitro compounds to the corresponding amines in good yield. 3 The method has been ap-plied successfullyto the reduction of 6-nitroindole to 6-aminoindole4 and to the conversion of a nitrosty-rylcolchicine ester to the corresponding amine. 5 Application ofthe method to nitro-6 or nitrosopyrim-idines7 gave anomalous products not readily char-acterized.It is apparent that the nature of the catalyst is not critical to the course of the reaction. Uniformly good yields of amines have been obtained using palladized charcoal8· 9 or platinum10 as the catalyst. Iron or copper powder also has been used, but the yields were inferior. 11 The catalytic effect may be merely the provision of a surface for reduction, since reduction products have been obtained using only porous tile as the catalyst. 12 However, no reduction took place without a catalyst at room or steam-bath temperatures. 3· 10· 13 The concentration of hydrazine appears to be the main factor controlling the nature and yields of re-duction products. If large volumes of alcohol and hence small concentrations of hydrazine hy-drate were used, amines were the sole products. If the hydrazine hydrate concentration was increased, good yields of intermediate products resulted; the