SU333835A1 - - Google Patents

Description

(54) METHOD FOR GETTING 1: TO THE PHOSPHATE OF AMINOHIPOLINE

J3 is hydroxyethyl, t is hydroxypropyl,

is that the compound of the general formula

The invention relates to the field of the bulk of new compounds, vinyl derivatives of the quinoline series, which are physiologically active and can be found in the pharmaceutical industry. It is known from the literature that the analgesic and - styryl derivatives of the quinoline series - possess high chemotherapeutic activity and are () acted out of a wide spectrum of action. The main method of obtaining - 4-amino quinoline derivatives is the interaction {stvie of 4-chloroquinoline derivatives with amishc. () C e) with an excess of amine or in the medium feiHo; ia. However, in these cases, the isolation of the target products presents great difficulties (1) O) 1, a significant tarring of the original n) and the yields are very small. G1) edlagpeps is a simpler method of obtaining new compounds of the hinnolin series: aminohnoline phosphates. j We propose a method for the production of phosphates (aminrhinoline of the general formula

A

.i () "- lolto, where ft, R, R" have the indicated values are subjected to interaction with the compound of the general formula HH ", where R has about" the specified values, in dimethylformamide medium at a temperature of preferably 140-15 ° C, followed by processing the obtained wherein the compounds are orthophosphoric acid and the isolation of the target product in a known manner. For a normal course of the reaction, a small excess of the starting amine is necessary, since an excess of the amine binds to release hydrogen chloride and the reaction proceeds towards the formation of the aminoquin derivative. The reaction proceeds with vigorous stirring for 8-15 hours. Example. Diphosphate 5 -nit (rofuryl-2) -vinyl-4 - (: 0-diethylamino.-methylbutylamino) -7-chlorochknolin. iK of a mixture of 3.35 g {0, 01 mol) | 4,7-dichloro-2g-C2 - 5-nitro | Reel 2) -vinyl-quinoline and 2.3 g (O, O15 mol) of 1-diethylaminopentane added 15 ml of dimethylformamide. The temperature of the reaction mixture is raised to 14 ° -150 ° C, heated at this temperature and vigorously stirred for 1 hour. The reaction mixture is cooled, poured into ZOO ml of chloroform, shaken vigorously and washed with water until neutral. The chloroform layer is anhydrous potassium carbonate and the solvent is distilled off in a water jet vacuum, the residue is dissolved in 250 ml of acetone; the base solution in acetone is passed through alumina, washed with acetone, and eluted with a sufficient amount of acetone. This solution is treated with 1% orthophosphoric acid solution to pH 3.5. The precipitated precipitate is filtered off, washed with acetone, sous shat in a vacuum desiccator over anhydrous calcium chloride. Found %: C 44.52; H 5.73; M 8.36; 1 5.92; R 9.14. 4 29 "4 3 - sR04 Calculated,%: C 44.14; H, 5.4O; N8.58; 1 5.4b; R 9.48. Similarly obtained: Diphosphate 2- | 2- 5-nitrofuryl-2) -B1 or 5 | -4- 3-hydroxyethylamino) -quinoline, yield 8, so pl. 82 ° C (decomposed). Found:% C 39, 4.51; N8.21; 12.11. W Calculated,%: C 39.16; H 4.06;,. Ov; 11.88.H (I Diphosphate 2- {2- (5-nitrofuryl-2) -VIN-4- (α-oxyethylamino) -7-chlorochinslin, yield 60.1%, mp 104 ° C (decomposed ) .I Found,%: C 37.01; H 3.16; N7.94; C1 6.72; R 11.53.,. Calculated,%: C 36.73, H 3.62; N7.56 ; C1 6.37; P 11D4., And, Diphosphate (5-nitrofuryl-2) -butadienyl-4- (JJ -oxyethylamino) -7-chloroquinoline, yield 51.9%, mp. - 105 ° C (decomposes) Found,%: C 39, OO; H 4, O2; W 7.20; C1 6; 51; P 11.10. 3 04Calculated,%: C 39.22; H 3,, 22; C1 6.09; P 10.64. Diphosphate (5-nitrofuryl-2) -vi (V-hydroxypropylamino) -7-chloroquinoline, yield 59.8%, mp: 1 ° C °., (Decomposed). Found ,%: C 38.11; H 4.09;, 63; C1 6.26; R 11.16.