SU405885A1 - METHOD FOR OBTAINING ETHER 7-METH) XI-8-DIALKYL-MINOMETHILROMON-2-CARBIC ACID - Google Patents

Description

one

The invention relates to a process for the preparation of new compounds, the esters of 7-methoxy-8 dialkylaminomethyl, chloro, monoH-2-carboxylic acid of the general formula

Cun

Sh

SNo

where R is alkyl; Ri and R2 are alkyl or Rj and Ra, together with the nitrogen atoms with which o «and svaye, form a heterocycle: a climatic ring, which can be interrupted by another nitrogen heteroatom, or their chlorohydrates with physiological activity.

It is known that in the interaction of chromone mono-2-carboxylic acid esters with amines pro. } 1 either ether amidation or amidation accompanied by splitting of the oxygen-containing cycle.

The proposed method is characterized in that the active amine does not affect the ester group and the carbon atom in the 2-position of the pyrone ring and makes it possible to obtain mesomethyl derivatives of chromone-2-carboxylic acid esters with 8 dialkyls.

The proposed method consists in the fact that the corresponding 7-methoxy-8-chloromethylchromone-2-karboxylate ester is reacted with an amine of the general formula

R,

HN

By

ten

where RI and Ra are as defined above, in an organic solvent medium, such as benzene, in the presence of triethylamine at a reaction temperature of the reaction mixture, and the desired product is isolated or converted into the hydrochloride using conventional techniques.

Example 1. 7-methoxy-8-pi1-peridinomethylchromone-2-carboxylic acid ethyl ester hydrochloride.

1.98 g (0.0066 mol) of 7-methoxy-8-chloromethyl chromone-2-carbonic acid ethyl ester, 0.69 g (0.0081 mol) of piridide, and 0.66 g (0.0066 mol) of triethylamine in 20 ml anhydrous benzene is boiled for 5 hours, the precipitate is filtered off, the filtrate is evaporated in vacuo, the residue is dissolved in 10% hydrochloric acid and the insoluble precipitate is filtered off. The filtrate is alkalinized with 10% sodium carbonate solution, the precipitated oil is extracted with benzene, the benzene solution is evaporated

the residue is again dissolved in benzene, an ether solution of hydrogen chloride is added, filtered and 1.1 g (43.5%) of the desired product are obtained, m.p. 181-il82 ° C (absolute olirt).

Found,%: C 59.59; 59.46; H 6.76; 6.67; C1 9.12; 9.17; N 3.64; 8.68.

C, 9H24C1N05.

Calculated,%: C 59.77; H 6.34; C1 9.28; N 3.67.

P. Example 2. Methyl dichlorohydrate of 7-methoxy-8-Y-1methyl piperazinomethylchromone-2-carboxylic Acid.

4 g (0.0124 mol) of 7-methoxy-8-chloromethylchromone-2-carboxylic acid methyl ester, 1.42 g (0.0124 mol of N-methylpyrierase and 1.52 g (0.015 mol) of triethylamine in 40 ml of anhydrous benzene: 5,5 hours are boiled, cooled, the precipitate is filtered off, the benzene solution is evaporated under vacuum, the residue is dissolved in benzene, ethereal chlorohydrogen solution is added to obtain 2.8 g (47.1%) of the desired product, so pl. 222-223 ° C (decomp., opirt).

Found,%: C, 51.85; 51.88; H 6.01; 6.0; C1 16.61; 16.50; N 6.25; 6.36.

CisHs CbNaOs.

Calculated,%; C, 51.57; H 5.77; C1 16.91; N 6.68.

Example 3. Chlorine. Methyl ester of 7-methoxy - 8-diethyl1a: m.iH10met1Ilrhomon-2ka, p bani.ovoy acid.

4.25 2 (0.015 mol of 7-methoxy-8-chloro-methyl-methyl-2-carboxylic acid methyl ester, 1.1 g (0.015 mol) of diethyl) mine and 1.52 g (0.015 mol) of triethylamine in 40 ml anhydrous benzene is boiled for 6 hours, the precipitate is filtered off, the filtrate is evaporated in a vacuum, the residue is triturated with a small amount of ether, the precipitate is filtered off, converted into chlorine hydrate in the usual way and 1.4 g are obtained.

(26.6%) of the desired product, so l. 190 ° C (decomp., Tart).

Found,%: C 57.43, 57.27; H 6.28, 6.40; C1 10.25, 10.27. CirHasClNOs.

Calculated,%: C 57.38; H 6.23; C1 9.97.

Subject invention

Method for preparing 7-methoxy-8-dialk, ilaminomethyl-chromo-1H-2-carbonoxy acid esters of the total form:

COOK

Shyo b to

-RI SNg-NC

R-i

where R is alkyl; Ri and Ra are alkyl or Ri and -R2, together with the nitrogen atom, are linked with ayorim, form a heterocyclic ring that can be interrupted by another heteroatom of nitrogen, or their chlorohydrates, characterized in that the corresponding 7-methoxy8 ether is chloromethylchromone - 2-carboxylic acid is reacted with an amine of the general formula

.x

HN

Ig

where RI and R2 are as defined above, in an organic solvent medium, for example benzene, in the presence of triethylamine at the boiling point of the reaction mixture, and the desired product is isolated or converted into the hydrochloride using conventional techniques.