Salicylic acid 5-chloro

The 4-chloro-5-sulfamyl salicylic acid used as starting point was prepared in the following way ... 

The unequivocal proof is furnished by the crystal inclusion behavior of simple 2-hydroxy-3-naphthalenecarboxylic acid 25a46 , and its 1-chloro derivative 25b37 since both allow the formation of a crystalline adduct ( clathratocomplex 19)) with dimethylformamide with the expected 1 1 stoichiometric ratio37. Thus, the salicylic acid function (2-hydroxycarboxylic acid group) is shown to be an excellent sensor, or a good complementary site for the dimethylformamide molecule in solid state inclusion. 

Niclosamide was synthesized industrially by first chlorinating salicylic acid in chlorobenzene to yield 5-chlorosalicylic acid (I). Control of the amount of chlorine introduced is essential at this step, because an excess halogen leads to the formation of 3,5-dichlorosalicylic acid in addition to (I). When (I) is heated with 2-chloro-4-nitroaniline (II) in chlorobenzene (102— 104°C) in the presence of phosphorus oxychloride, niclosamide (III) is obtained [7]. 

Methanogenic enrichments resulted in O-demethylation of Dicamba to 3,6-dichlorosalicylic acid which was reductively dechlorinated to 6-chloro-salicylic acid and to salicylic acid, which was in turn further degraded to CH4 and C02. 

Determination of various analgesic and antipyretic pharmaceuticals on reversed phase has included not only the analysis of serum levels of aspirin, salicylic acid and salicyluric acid using acidified acetonitrile (557), or methanol (338), but also suUinpyrazone under isocratic conditions (339), and 6-chloro-a-methylcarbazole-2-acetic acid (340). The polar thiol metabolites of acetaminophen were analyzed by RPC and the method was found to be superior to other chromatographic techniques used in this analysis (341). 

Prepd from 3-chloro-5-amino-salicylic acid and Na-nitrite in dil.HCl. Explodes at 193°... 

A number of 5//-l,4-benzodioxepin-ones and -diones have been prepared (72HC(26)319, p. 339). The reaction of the sodium salt of salicylic acid with 2-chloroethanol gave (269) (75BSF(2)277) and treatment of the methyl ester of 2-acetyl-6-chloro-3,5-dimethoxyphenoxyacetic acid with 3M hydrochloric acid gave (270). The dione (271) was prepared by heating 2-carboxy-5,6-dimethoxyphenoxyacetic acid in acetic anhydride and (272) was prepared from chloroacetylsalicylic acid. 

Diazosalicylic acid and derivs 5 D1175 3-chloro 5-diazosalicylic acid 5 D1175 3-chloro-5-diazosalicylic acid 5 D1175 3-diazo-5-nitro-salicylic acid 5 D1175... 

Aminopyridine can be prepared by the reaction of 4-chloro-l,3-benzoxazines (47) with pyridine TV-oxides. Here it is proposed that an ion or radical pair is formed initially, which through displacement of hydrogen chloride and rearrangement leads to an TV-substituted benzoxazine (48). Finally, acid hydrolysis gives 2-aminopyridine and salicylic acid (49 Scheme 14) (80CPB465). 

A mixture of 5-chloromethyl salicylate, 3-chloro-2-methylpropene, potassium carbonate, and acetone was heated at reflux overnight. After cooling, the mixture was extracted with diethyl ether and ethyl acetate. The organic extracts were combined, washed twice with a 10% sodium chloride solution and water, dried over sodium sulfate, and concentrated in vacuum. The resulting liquid was vacuumed distilled. The fraction collected and the desired 5-chloro-2-(2-methyl-2-propenyloxy)benzoic acid, methyl ester was obtained. 

Activated aromatic compounds are chlorinated readily by (dichloroiodo)benzene. Generally, negligible amounts of ortAo-chloro isomers are produced from diverse aromatic compounds, e.g. salicylic acid gave its 5-chloroderivative (89%) [16]. Exceptions were noted in the chlorination of the triphenyl phosphinimine of aniline which afforded o- and p-products in the ratio 7 3 [17], and of 2-naphthol which gave its 1-chloroderivative (84%) [16]. (Dichloroiodo)benzene was superior for the chlorination of uracil bases and protected nucleosides, e.g. [18] ... 

The only practical methods for the preparation of o-chloro-benzoyl chloride to be found in the literature consist in the treatment of o-chlorobenzoic acid with phosphorus penta-chloride1 or thionyl chloride.2 It has, however, also been formed by distilling salicylic acid or its sodium salt with phosphorus pentachloride,3 and by heating the dichloride of o-sulfobenzoic acid.4... 

Copper complexes (152) of o-hydroxy-o -(p-aminoethylamino)diarylazo compounds have been prepared ° by the reaction of the corresponding o-chloro-o -hydroxydiarylazo compounds and ethylenediamine in the presence of copper(II) ions (c/. Section 58.2.3. l(iii)(c)). Dyestuffs of this type have been evaluated on nylon but are reported to have very poor fastness properties. Copper complexes such as (153) have been preparedby similar methods. Other, related tetradentate diarylazo compounds, e.g. (154), (155) and (156), are obtained by the reaction of a suitable diazonium salt with the appropriate diarylamine. Chromium(III) and cobalt(III) complexes of dyes of this type, in which the coordination sphere of the metal is completed by a colourless bidentate ligand such as ethylenediamine, salicylic acid or 8-hydroxyquinoline, are reported to have dyeing properties on wool similar to those of the comparably charged 2 1 complexes derived from tri-... 

The fact that the presence of the hydroxy function originating from the salicylic acid is an essential requirement for cestodicidal and flukicidal activity, led Hoechst scientists to prepare a variety of 2,6-dihydroxybenzoic acid anilides. The most effective compound of the series were 4 -chloro/bromo-6-hydroxysalicy-lanilides (5a,b). Of these, the bromo analogue, called resorantel (terenol, 5b) was found to be more effective than the 4 -chloro analogue (5a) [12]. Resorantel was later... 

Analgesic and antiinflammatory drugs Analgesics Salicylic acid, aspirin, caffeine, butalbarbitone, phenacetin, p-chloro-acetanilide, in a multi-component analgesic product Partition p Bondapak C18 0.01% aqueous ammonium carbonate/ acetonitrile (60 40)... 

Direct introduction of a solubilizing function can be achieved by carboxylation and by sulfonation. The historical example of carboxylation is the Kolbe synthesis of salicylic acid. Sulfonation was employed to solubilize guaiacol, camphor and 7-chloro-8-hydroxyquinoline (Fig. 36.1). 

---