Anilines pharmaceutical

Occurs in the high-boiling fraction of coal tar. Most conveniently prepared by Skraup s reaction by healing a mixture of aniline, glycerol, sulphuric acid and nitrobenzene. Used in the manufacture of dyestuffs, and pharmaceutical products. 

The major uses of aniline are in the manufacture of polymers, mbber, agricultural chemicals, dyes and pigments, pharmaceuticals, and photographic chemicals. Approximately 67% of the wodd production of aniline is used in the manufacture of rigid polyurethanes and reaction-injection-molded (RIM) parts for the constmction, automotive, and durable goods industries. 

Nitration of benzene yields nitrobenzene, which is reduced to aniline, an important intermediate for dyes and pharmaceuticals. Benzene is chlorinated to produce chlorobenzene, which finds use in the preparation of pesticides, solvents, and dyes. 

Aniline (amino benzene) QH5NH2 Agrochemicals, dyes and pigments, pharmaceuticals, photographic chemicals, polymers, rubbers... 

The largest user of phenol in the form of thermosetting resins is the plastics industry. Phenol is also used as a solvent and in the manufacture of intermediates for pesticides, pharmaceuticals, and dyestuffs. Styrene is used in the manufacture of synthetic rubber and polystyrene resins. Phthalic anhydride is used in the manufacture of DMT, alkyd resins, and plasticizers such as phthalates. Maleic anhydride is used in the manufacture of polyesters and, to some extent, for alkyd resins. Minor uses include the manufacture of malathion and soil conditioners. Nitrobenzene is used in the manufacture of aniline, benzidine, and dyestuffs and as a solvent in polishes. Aniline is used in the manufacture of dyes, including azo dyes, and rubber chemicals such as vulcanization accelerators and antioxidants. 

Virtually all of the nitrobenzene made is converted to aniline. The most important use of aniline is for the preparation of 4,4 -diaminodiphenyl methane (commonly called methylenedianiline or MDA), an intermediate to one of the main ingredients used to make polyurethane foams and rubber. Aniline is also used to make other rubber chemicals, textile fiber intermediates, dyes, and pharmaceuticals. 

Nitro aromatics owe their great importance in organic synthesis for being intermediates for the generation of the respective anilines by hydrogenation [17, 61]. For instance, pharmaceuticals are produced via that route [61],... 

In 1978, Sugasawa et al., at Shionogi Pharmaceutical Co. reported ortho-selective Friedel-Craft acylation with free anilines with nitrile derivatives [4]. Sugasawa reported that the reaction requires two different Lewis acids (BC13 and A1C13) and does not proceed when N,N-dialkyl anilines are used. He proposed that boron bridging between nitriles and anilines led to exclusive ortho-acylation but a conclusive mechanism was not elucidated. The report did not offer any reason why two different Lewis acids were required and why the reaction did not progress with N,N-dialkyl anilines. Therefore, we initiated mechanistic studies. 

Alicyclic amines are used as pesticides, plasticizers, explosives, inhibitors of metal corrosion and sweetening agents as well as having uses in the pharmaceuticals industry. Aniline hydrogenation has been studied in the literature with the main reaction products cyclohexylamine, dicyclohexylamine, A-phenylcyclohexylamine, diphenylamine, ammonia, benzene, cyclohexane, cyclohexanol and cyclohexanone [1-9], The products formed depend on the catalyst used, reaction temperature, solvent and whether the reaction is performed in gas or liquid phase. For example high temperature, gas-phase aniline hydrogenation over Rh/Al203 produced cyclohexylamine and dicyclohexylamine as the main products [1],... 

A variety of natural products and pharmaceutical agents contain a tetrahydroquinoline moiety [31]. Recently, a simple and general access to these heterocycles by a so-far unknown domino reaction of aromatic nitro compounds 7-65 and 2,3-dihydrofuran mediated by indium in water has been described by Li and coworkers (Scheme 7.19) [32]. It is assumed that the process is initiated by reduction of the nitro group in 7-65 to give the aniline 7-66 on treatment with indium in... 

The title compounds, which are of pharmaceutical interest, are easily obtained in a one-pot procedure as a result of the formal amidation of malonic ester derivatives with an aniline followed by the cydization of the intermediate malondianilides [102] (Scheme 8.73). 

Aniline is an aromatic amine used in the manufacture of dyes, dye intermediates, rubber accelerators, and antioxidants. It has also been used as a solvent, in printing inks, and as an intermediate in the manufacture of pharmaceuticals, photographic developers, plastics, isocyanates, hydroquinones, herbicides, fungicides, and ion-exchange resins. It is produced commercially by catalytic vapor phase hydrogenation of nitrobenzene (Benya and Cornish 1994 HSDB 1996). Production of aniline oil was listed at approximately 1 billion pounds in 1993 (U.S. ITC 1994). Chemical and physical properties are listed in Table 1-2. 

Since its initial discovery by Michael Faraday in 1825,58 benzene (C6H6) has been recognized as an extraordinary substance. The spectacular properties of benzene and its derivatives (particularly the aniline dyes discovered by W. H. Perkin) initiated dramatic growth of the pharmaceutical, dyestuff, and munitions industries in the mid nineteenth century. The famous puzzle of the chemical structure of benzene was solved in 1865 by August Kekule in terms of two alternative six-membered-ring formulas ... 

The reduction of aromatic nitro-compounds is of exceptionally great interest, not only scientifically, hut also technically. The conversion of the hydrocarbons of coal tar into useful products began with the discovery of the nitration process the conversion, on the technical scale, of the nitro-group of nitrobenzene into the amino-group gave aniline, the starting material for the preparation of innumerable dyes and pharmaceutical products to aniline were added the homologous toluidines, xylidines, naphthylamines, and so on. 

Aniline is a purple dye that has the distinction of being the first synthetic dye ever made. It was developed in Germany at the end of the 19th century and its manufacture led to the development of the entire synthetic chemical and pharmaceutical industry that we know today. It is used as a dye and also as a stage in the synthesis of other dyes and chemicals. Unfortunately, both aniline and its derivatives, such as monomethyl-analine and dimethylaniline, are toxic. 

The relative importance of N-substituted arylamines for the construction of biologically significant molecules, particularly pharmaceuticals and agrochemicals, prompted the extension of rhodium-catalyzed allylic amination to aniline nucleophiles (Tab. 10.6) [41, 42]. The N-arylsulfonyl-protected anihnes were again optimal for high selectivity, analogous to that observed with the N-toluenesulfonyl-N-aLkylamines. 

Jenke [73] studied the extractabihty of aniline, diphenylguanidine, dedenzyl-amine, and triisopropanolamine from a synthetic polyisoprene rubber similar to the material used in pharmaceutical applications. Rubber samples were autoclaved (121 °C) in contact with water or NaCl 0.9% solution for lh.Table 33 presents the concentration of each compound in solution after the extraction procedure using 2g rubber material. Extraction profiles ranged between 1.64 and 3.73 mg/L, with the exception of diphenylguanidine, whose extraction yield reached 11.76 mg/L. 

Nitrobenzene and nitrotoluenes that are manufactured are converted to aniline, isocyanates, and other products used in the production of dyes and pharmaceuticals. 

Aniline has been un important raw material for many years. Used mainly in the vulcanization of rubber and in dyes, aniline has found uses tn the manufacture of hydro-qumonc. various pharmaceuticals, resins, and isocyaiutes Aniline is produced from nitrobenzene, from chlomhcn/cnc, and from phenol... 

Nitroaromatic compounds (NACs) are one of the widespread contaminants in the environments. Sources of NACs are numerous they originate from insecticides, herbicides, explosives, pharmaceuticals, feedstock, and chemicals for dyes (Agrawal and Tratnyek, 1996). Under anaerobic conditions, the dominant action is nitro reduction by zero-valent iron to the amine. Other pathways do exist, such as the formation of azo and azoxy compounds, which is followed by the reduction of azo compounds to form amines. Also, in addition to the possibility of azo and azoxy compounds, phenylhydrox-ylamine may be an additional intermediate (Agrawal and Tratnyek, 1996). Nitrobenzene reduction forms the amine aniline. Known for its corrosion inhibition properties, aniline cannot be further reduced by iron. Additionally, it interferes with the mass transport of the contaminant to the surface of the iron. The overall reaction is as follows ... 

To synthesize these pharmaceutically interesting compounds, metha-nolic solutions of acetic acid 6 (2.0 eq.)/2-formylbenzoic acid 7 (1.0 eq.) and aniline 8 (2.0 eq.)/potassium cyanide 9 (1.2 eq.) were introduced into the reactor from separate inlets, thus ensuring the formation of HCN and the... 

In addition to the examples provided, the authors also demonstrated the use of anilines and aliphatic amines as substrates, reporting isolated yields ranging from 65 to 98% (see Section 3), whereby this methodology is demonstrated for the synthesis of the pharmaceutically important molecules rimonabant (72) and efaproxiral (73) (Schemes 65 and 66, respectively). 

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