SU1351928A1 - Method of obtaining derivatives of hydroquinoline - Google Patents

Abstract

The invention relates to heterocyclic compounds, in particular, to the preparation of 1,2,3,4-tetrahydroquinoline derivatives (THC) of the formula: where R, Rj is H, R, is 2-COOH; R, R ,, - H, R, - 3-COOH; R, R, - H, 4-COOH; R, Rj-H, R, 5-COOH; R, H,. R3 6-COOH; R, H, R, - 8-COOH; R, - CH3, R4 Rj - H; R, CH ,, R, - H, which can be used as intermediates in the synthesis of biologically active compounds. The goal is to simplify the process. The preparation of TGH derivatives is carried out by the reduction of the corresponding substituted quinoline by means of ammonium formate in an alcohol medium in the presence of palladium black as a catalyst. The method is simple in execution and makes it possible to obtain derivatives of THC with a good yield (67-97% j. 1 table. I (L 00 ate with y r

Description

1 I

The invention relates to an improved method for the preparation of derivatives 1, 2, 3,4-tetra. 1 ndrohi11olina of the general formula

 H, Rj 2-COOH R, - AND, R 3-COOH

Rj-H, R3 4-COOH

 H, R3 5-COOH H, R3 6-COOH

 H, R, 8-COOH

VII R, SNE,

R R - H

VIII R, R, - CH ,, R, H.

I4

increases recovery time; 1) The use of a larger amount of ammonium formate is inappropriate, i. since there is little effect on the yield and duration of the reaction.

All compounds are homogeneous by chromatography on 10 Silufol plates in the benzene-ethyl acetate-acetic acid solvent system (100: 50: 11.

Properties and yields of compounds I - VIII are presented in the table. 15 Thus, the proposed method is simple in execution and makes it possible to obtain the desired products with a good yield.

Claims (1)

20 claims The method of obtaining the derivatives of 1, 2,3, 4-tetrahydroquinoline of the general for-compounds can be used as industrial products in the synthesis of substances with a wide spectrum of biological activity. The purpose of the invention is to simplify the process. This goal is achieved due to the fact that the reduction of the substituted quinoline is carried out by means of ammonium formate in the presence of palladium black. Example. 1,2,3,4-tetrahydroquinolin-2,3-, 4-, 5-, 6-, 8-carbonic acids (I-VI). Mix 0.05 mol of 2-, 3-, 4-, 5-, 6- or 8-quinoline-carboxylic acid in 20 ml of methanol in the presence of 1 g of palladium black and 4. G formate ammonium for 15 hours at 20 ° C. The catalyst is filtered off, the mother liquor is evaporated, the residue is dissolved in chloroform, the filtrate is evaporated, passed through a short column c and derivatives I - VI. 5-metsh1-1,1,2,3,4-tetrahydroquinoline (VII) and 5,6-dimethyl 1,2,3,4-tetrahydroquinoline (VIII) are obtained similarly from 5-cyanquinoline and-5-cy- an-6-methylquinoline. In this case, simultaneously with the restoration of the ring, the transformation of the cyano group into the methyl one occurs. The use of a smaller amount of ammonium formate reduces the yield and 25 mules 30H where I R, H, R, 2-COOH I I R, H, R, 3-COOH IIIR, Rj- H, R ,, 4-COOH IVR, H, R, 5-COOH V R, H, R3 6-COOH VIR, H, R, 8-COOH VIIR CH ,, R R, - H VIIIR, CH, R3 H, by reducing the substituted quinoline c. the presence of a heterogeneous catalyst in an alcohol medium, characterized in that, in order to simplify the process, quinolines of general formula II are reduced 1R, R, - M, K, 2-COOH 2R, R.- AND, R3 3-COOH 3R, R, - H, R, 4-COOH 4R, H, R 5-COOH 5R | H, R, 6-COOH 6 R, H, Rj 8-COOH 7 R, Rj-H ,, R2 CH 8 R, H, R, -CH, R 6-CH, the reduction process is carried out by means of ammonium formate and palladium black is used as a catalyst.