Dinitronaphthalenes synthesis

Nitration via diazotisation has been extensively used for the synthesis of isomeric dinitronaphthalenes. Ward and co-workers used nitration via diazotisation to prepare 3,3, 4,4 -tetranitrobiphenyl from 3,3 -dinitrobenzidine, and 3,4,5-trinitrotoluene from 3,5-dinitro-4-toluidine. Ward and Hardy " prepared 1,4,6-trinitronaphthalene from 4,7-dinitro-1-naphthylamine. Korner and Contardi used the nitrate salts of aryldiazonium compounds for the synthesis of polynitro derivatives of benzene " and toluene. " " Accordingly,... 

Probtem 18.63 Synthesize from naphthalene and any other reagents (a) naphthionic acid (4-amino-l-naphthalenesulfonic acid), (b) 4-amino-l-naphthol, (c) 1,3-dinitronaphthalene, (d) 1,4-diaminonaphthalene, (e) 1,2-dinitronaphthalene. Do not repeat the synthesis of any compound. ... 

The first information (37JGU739 67CB2164) about the synthesis of 1,2-dihydrobenzo[crf]indazole by reduction of 1,8-dinitronaphthalene or naphtho[equilibrium with 1,3- and l,5-dihydrobenzo[c[Pg.43]

Aromatic diazonium salts on treatment with sodium nitrite decompose to form nitro compounds. This method represents a good procedure for obtaining o- and p-dinitrobenzenes, in 70% and 76% yield, respectively, from the corresponding diazonium sulfates. Improved yields in the preparation of dinitronaphthalenes are obtained when the decomposition of the diazonium sulfates is catalyzed by a cupro-cupri sulfite prepared by the interaction of copper sulfate and sodium nitrite. The procedure is illustrated by the synthesis of 1,4-dinitronaphthalene (60%). Occasionally, diazonium fluoborates are first formed, and these compounds are treated with sodium nitrite in the presence of copper powder, viz.,... 

Some kinds of proton sponges are best prepared starting from accessible l,8-bis(methyl-amino)naphthalene (4) or its derivatives2,40-43. For example, the optimal synthesis of l,8-bis(dimethylamino)-4,5-dinitronaphthalene (51) consists in methylation of compound 50, which in turn can be prepared from perimidone 49 (Scheme 2)44,45. 

Scheme 45 Synthesis of benzo-fused isoindoles from dinitronaphthalenes...

Synthesis Pfaltz Bauer http //www.pfaltzandbauer.com-, SNPE Chimie http //www.snpe.com, TCI Am. http //www.tciamerica. com 1,8-Dinitronaphthalene CAS 602-38-0 EINECS/ELINCS 210-016-1 UN 8027... 

The potential of microreaction processes to influence isomeric product distributions was demonstrated by Loebbecke et cd. [20], They reported on the nitration of naphthalene at moderate temperatures in different types of microreactors to ensure isothermal processing and precise control of residence time (Scheme 4.8). A deliberate synthesis of either mono- or dinitro-substituted naphthalene with high selectivities was achieved, in contrast to a broad product spectrum obtained rmder macroscopic batch conditions. In particular, isomeric ratios of 1- to 2-mononitro-naphthalene and also 1,5- to 1,8-dinitronaphthalene could be significantly increased compared with batch processes. 

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