A second form of 6 6′-dinitrodiphenic acid, and its conversion into new cyclic systems
A second form of 6 6′-dinitrodiphenic acid, and its conversion into new cyclic systems
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DOI：
10.1039/ct9211900593
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发表时间：
1921-01-01
期刊：
影响因子：
--
通讯作者：
Stubbings, WV
中科院分区：
文献类型：
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作者：
Kenner, J;Stubbings, WV
结合另一项研究，制备6：6‘-二硝基二苯酸变得可取。该化合物首先由Schulze(Annulen，1880,203，95)作为联苯二酸硝化的产物之一，也是由菲醌得到的二硝基衍生物的混合物氧化得到的。它的可能的组成，虽然由Schad(Ber.，1893，26,219)承认，但首先由Schmidt(Ber.，1903，36,3745)证明，他通过蒸馏钡盐从它制备2：2‘-二硝基联苯，并以类似的方式从相应的二氨基酸获得咔唑，这是Schad(Zoc.如图所示)已经做好了准备并确定了特征。然而，酸的合成还没有进行，因此我们建议通过合成材料来完成刚刚总结的证据。2-氯-3-硝基苯甲酸是用稀硝酸氧化2-氯-3-硝基苯甲酸得到的，而相应的碘酸的制备是我们最近报道的(T.，1920,117,776)。这两种酸中的任何一种的酯，但最好是后者的酯，很容易与铜粉反应，并提供所需酸的酯：
IN connexion with another investigation, it became desirable to prepare 6: 6'-dinitrodiphenic acid. This compound was first obtained by Schulze (Annulen, 1880, 203, 95) as one of the products of nitration of diphenic acid, and also of oxidation of the mixture of dinitro-derivatives obtained from phenanthraquinone. Its probable constitution, although recognised by Schad (Ber., 1893, 26, 219), was first demonstrated by Schmidt (Ber., 1903, 36, 3745), who prepared 2: 2'-dinitrodiphenyl from it by distillation of the barium salt, and obtained carbazole in a similar manner from the corresponding diamino-acid, which Schad (Zoc. cit.) had prepared and characterised. The synthesis of the acid had, however, not been carried out, and we therefore proposed to complete the evidence just summarised by preparing our material synthetically. 2-Chloro-3-nitrobenzoic acid was obtained by oxidation of 2-chloro-3-nitrotoluene with dilute nitric acid, whilst the preparation of the corresponding iodo-acid has recently been described by us (T., 1920, 117, 776). The esters of either of these acids, but preferably of the latter, reacted easily with copper powder, and furnished the esters of the desired acid: