6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxalines are important class of heterocyclic compounds, associated with wider pharmacological applications. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Formula: C8H5ClN2
Action of o-phenylenediamines upon dihydroxytartaric acid was written by Chattaway, Frederick D.;Humphrey, William G.. And the article was included in J Chem. Soc. in 1929.Formula: C8H5ClN2 This article mentions the following:
When Na dihydroxytartrate is heated with aqueous o-C6H4(NH2)2, 2 mols of the diamine react with 1 mol. only of the salt, forming quinoxaline-2,3-dicarboxy-o-phenylenediamide (I); Na dihydroxytartrate is only very sparingly soluble in H2O and any excess above 1 mol. remains in suspension unchanged. When the filtered alk, solution is partly neutralized with HCl, I seps. as a colorless crystalline powder, stable in neutral solution and dissolving readily in cold dilute aqueous alkali, from which it is reprecipitated on addition of a deficiency of acid. It dissolves in hot dilute HCl (1:50), but on cooling, the o-phenylenediamine salt, (II) of quinxaline-2,3-dicarboxylic acid (III) seps; whereas, if it is dissolved in hot moderatelv concentrated HCl (1:1), III separated on cooling o-phenylenediamine-HCl remaining in solution The II and III may consequently be obtained directly from the original yellow condensation solution, the former by making the solution weakly acid with HCl, and the latter by saturating it with gaseous HCl. Attempts to acetylatc or benzoylate I by the usual methods also cause decomposes, with formation of the di-Ac or the di-Bz derivative of o-C6H4(NH2)2. Heated with Ac2O, III yields the anhydide, while dry NH3 on this anhydride in C6H4 suspensions gives the NH4 salt of 3-carbamylquinoxaline-2-carboxylic acid (IV), from which the acid itself may be obtained on acidification. This amic acid is converted into the corresponding imide (V) on being heated above its m. P., and into the Ac derivative of the imide on boiling with Ac2O. On being heated above its m. p., III decomposes, evolving CO2 and yielding a small quantity (10%) of quinoxaline; better yields (30%) of this base are obtained by heating the NH4 salt of the acid. In common with other N bases, quinoxaline forms a stable, well-crystallized monotetrachloroiodiede. Similarly, Na chloroquinoxaline-2,3-dicarboxy-p-chloro-o-phenylenediamide, from which the p-chloro-o-phenylenediamine salt of 6-chloroquinoxaline-2,3-dicarboxylic acid, and the free acid (VI) are obtained by heating with dilute and with concentrated HCl, resp. p-Bromo-o-phenylenediamine gives the corresponding Br derivative These halogen-substituted derivatives are considerably less soluble than the unsubstituted compounds, and are therefore more readily prepared and purified; otherwise their reactions are analogous. The following compounds were prepared and characterized: I, m. 184° (decomposition). II, lemon-yellow, m. 186° (decomposition). III, prisms containing 2 mols. H2O of crystallization, m. 190° (decomposition after loss of H2O at 110°); Et ester, C14H14O4N2, prisms, m. 83°; NH4 salt, m. 220-30°; anhydride, pale yellow prisms decomposing and charring 250-60°. IV, m. 190-5° (decomposition). V, pale yellow, m. about 260° (decompose); Ac derivative, leaflets, m. about 220° (decomposition). Quinoxaline mono-tetrachloroiodide, C6H4N2. HICl4, m. 125-30° (decomposition). 6-Chlroquinoxaline-2,3-dicarboxy-p-chloro-o-phenylenediamide, C16H8O2N4Cl2, m. 207° (decomposition) (p-chloro-o-phenylenediamine salt, C16H18O4N4Cl3, m. 205° (decomposition)); 6-bromoquinoxaline-2,3-dicarboxy-p-bromo-o-phenylenediamide, m. 198° (decomposition) (p-bromo-o-phenyleneamine salt, m. 199° (decomposition)). VI, m. 175° (decomposition) (anhydride,m. 235-40° (decomposition), Et H ester, m. 159°; di-Et ester, m. 60°; NH4 salt, m. 215-25° (decomposition)). 6-Chloroquinoxaline, m. 60°, 6-Bromoquinoxaline-2,3-dicarboxylic acid, m. 172° (decomposition) (anhydride, m. 235-45° (decomposition), Et H ester, m. 161°, di-Et ester, m. 69°, NH4 salt, m. 235-40° (decomposition)). 6-Bromoquinoxaline, m. 56°. Pyrazinetetracarboxylic acid (by oxidation of the anhydride of III), m. 205° (decomposition), di-K di-H salt is crystalline, tetra-Et ester, m. 104°. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Formula: C8H5ClN2).
6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxalines are important class of heterocyclic compounds, associated with wider pharmacological applications. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Formula: C8H5ClN2
Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider