The method of obtaining 2-alkyl - and phenyl-5,10-dihydrophenazine


C07D241/46 - Phenazines

 

(57) Abstract:

The invention relates to a method for producing 2-alkyl - and phenyl-5,10-dihydrophenazine General formula (1), where R is H, (CH3)3C-; C2H5(CH3)2C-; CH3(C2H5)2C-; cyclo-C6H11- and 2-3-phenyl, by heating a mixture of ortho-phenylenediamine and the corresponding allylpyrocatechol or 2,3-dihydroxynaphthalene. The method differs in that the mixture having the molar ratio of the components is 1:1, heated at 55-105oC to stop the sublimation of the reaction product. The invention reduces labor costs by simplifying the method, cheaper source of substances that increase the speed of the process and output of products, improve the monitoring process and to obtain a wide range of compounds, which find extensive applications in organic chemistry and redox processes. table 2.

Applying a new method of obtaining compounds of General formula

< / BR>
where R is H; (CH3)3C-; C2H5(CH3)2C-; CH3(C2H5)2C-; cyclo-C6H11- and 2-3-phenyl. The invention relates to organic chemistry and can be used in the synthesis of derivatives of phenazine, cattelino-reduction potentials 0,05-0,30 [Indicators. So 2. Ed. by E. Bishop, M.: Mir, 1976 S. 71].

The known method of synthesis methoxyfenozide from methoxypyridine and ortho-phenylenediamine through an intermediate stage of oxidation methoxypyridine up methoxy-ortho-benzoquinone [Syntheses of organic products. Collection 4.- M: IL, 1953, c. 422].

Closest to the proposed method is the method of condensation of the methoxy-ortho-benzoquinone with ortho-phenylenediamine [Syntheses of organic products. Collection 4.- M: IL, 1953, c. 422].

As a prototype of the selected closest to the original substances and technical execution method of condensation [the above compilation 4]. The main disadvantage of the prototype is the stage of oxidation of the derived pyrocatechin to the corresponding ortho-benzoquinone using a large excess of oxidant. The second disadvantage is the high consumption of the condensing agent, as well as large quantities of solvent (poisonous benzene) and purifying and brightening agents (aluminum oxide and activated birch coal). The disadvantages include mnogovershinnoe process and low yield of the target product.

The aim of the invention is to reduce labor costs by simplifying the method, given the ECCA and receive a wide range of compounds, finds extensive applications in organic chemistry and redox processes.

This goal is achieved by mixing equimolar quantities of ortho-phenylenediamine, ortho-dihydroceramides connection (pyrocatechin or 4-allylpyrocatechol, or 2,3-dihydroxynaphthalene) and heated at a predetermined temperature. The condensation product purified by sublimation at atmospheric pressure.

The method differs from the method, selected as a prototype, the fact that there is no condensing agent, excluded phase oxidation derived pyrocatechin in the corresponding ortho-benzoquinone, do not apply solvents and other auxiliary reagents. The absence of a condensing agent is necessary because condensation with ortho-phenylenediamine of pyrocatechin, allylpyrocatechol and dihydroxynaphthalene flows under the influence of temperature and the condensing agent is not needed. The resulting derivative 5,10-dihydrophenazine easily lose their hydrogen into the corresponding derivative phenazine (this is based redox processes with their participation). The absence of an intermediate stage of oxidation allylpyrocatechol in alkyl-ortho-benzoquinoines is determined by the fact that quinones are not needed on the on the, the final products are purified by sublimation. In General, all these differences from the prototype lead to the fact that the proposed method is a General method of synthesis of a broad range of compounds and can easily become an industrial method of obtaining them because of the simplicity, cheapness and safety.

Example (General method).

Mix 0.01 mol of ortho-phenylenediamine and 0.01 mol of pyrocatechin or 4-allylpyrocatechol or 2,3-dihydroxynaphthalene (see tab. 1). Mix thoroughly powdered and placed in a device for sublimation at atmospheric pressure. Slowly (over hours) heat the mixture until a homogeneous liquid melt. From the melt at the temperature indicated in the table. 1, begins to vothonas product of condensation. Maintaining the specified temperature (external heater), sublimation lead to the complete transformation of the melt in a pure substance. It is not recommended to increase the reaction temperature or the temperature of sublimation, this leads to partial resinification of the melt and reducing product yield. The yields of products in the table. 1, and the melting temperature is given for substances treated with a single sublimation. Systematic names of products and analyses of these compounds are presented in table. 2 under Lavinia which are listed in the table. 1.

The method of obtaining 2-alkyl - and phenyl-5,10-dihydrophenazine General formula (1)

< / BR>
where R is H; (CH3)3C-; C2H5(CH3)2C-; CH3(C2H5)2C-; cyclo-C6H11- and 2-3-phenyl,

by heating a mixture of ortho-phenylenediamine and the corresponding allylpyrocatechol or 2,3-dihydroxynaphthalene, characterized in that the mixture having the molar ratio of the components is 1:1, heated at 55 - 105oC to stop the sublimation of the reaction product.

 

Same patents:
Up!