SU389091A1 - METHOD OF OBTAINING 2-BENZ-AND-INDOLINYLUXE - Google Patents

Description

one

The present invention relates to a process for the preparation of novel derivatives of indolyl acetic acid, which are used as biologically active substances, and that also in other areas of the chemical industry.

It is known to obtain derivatives of indole acetic acid by catalytic reduction of esters of "pdolyl acetic acid, followed by saponification with sulfuric acid.

However, the synthesis of starting indolylacetic acids is rather complicated, expensive catalysts (platinum oxide) are used for hydrogenation, and the reduction reaction proceeds slowly.

For the preparation of 2-benz-y-indolyl acetic acid, 3-chloro-1,2,3,4 tetrahydrobenzo- / g -nnoline or its mixture with 2- (chloro, rmethyl) -benz-indol1in is offered with potassium cyanide in DMSO and the subsequent spraying of the 2-benz-indoline-acetic acid nitrile formed by known methods, for example, in the presence of hydrochloric acid and the treatment of 2-benzo-nitrochloride hydrochloride with sodium acetate.

2- (Chloromethyl) -beiz-y-indoline is formed by boiling 3-hydroxy-1,2,3,4-hydrochloride tetrahydrobenzo- / g -quinoline hydrochloride with phosphorus.

Example 1. 22.0 g (0.1 mol} 3-chloro, 2,3,4 - tetrahydrobenzo / g-quinoline, 13.0 g

(0.2 mol of potassium cyanide, 80 ml of DMSO and 20 ml of water, unmixed, are heated for 1.5-2 hours at 140-150 ° C, diluted with water and extracted with ether or another organic solvent. After removing the solvent, nitrile 2 - benz-α-indyl acetic acid was boiled for 1 hour with 200 ml of hydrochloric acid ((1.17), cooled to (-5) - (-10) ° C, the crystals formed were filtered and treated with an aqueous solution of 78.0 g ( 0.1 mol of sodium acetate. The precipitate is poured with water and dried. The yield of 2-benzo-n-dinol-acetic acid is 13.6 g (60%), mp 108.0-109.3 ° С (ethanol is «-hexane , 1: 9).

Found,%: N 13.4; 13.2.

C | J-Ii2N2.

Calculated,%: N 13.4.

Example 2. 47.0 g (0.2 mol) of 3-hydroxy hydrochloride - 1,2,3,4-tetrahydrobenzene / g -H1 Inolina and 46 ml (0.5 mol} chlO | pO | Kisi phosphorus boil I hour, poured on ice, the crystals formed are filtered off, washed with water and shaken with a BODN solution of sodium carbonate in the presence of an organic solvent, such as efnr. - / 1 -quinoline n 2- (chloromethyl) -benzene indoline) is treated, as in Example 1, with cyanium, then hydrochloric acid and sodium acetate. 3 Output 2-benz-I-indolinyl xacetic acid, 26.0 g (57%) in terms of 3-hydroxy-1,2,3,4-tetrahydrobenzo-1-quinoline hydrochloride. Subject of the invention s The method for preparing 2-benz-g-indolinylacetic acid, characterized in that 4 3-chloro-1,2,3,4-tetrahydrobenzo-1 / quinoline or its mixture with 2- (chloromethyl) -be, 113-g-indoline is heated with potassium cyanide in dimethyl sulfoxide, followed by nitrate Aryl 2-Be 3- - pdolynylacetic acid in the target product with different methods.