SU210173A1 - METHOD FOR PRODUCING CHLORHYDRATES OF AMINO ALKYL ETHER 3-SUBSTITUTED 4-PHTHALAZONE-1-CARBONIC ACID - Google Patents

Description

The invention relates to the field of the preparation of compounds which can be used in the synthesis of biologically active substances.

The proposed method for the preparation of aminoalkylObid chlorohydrates of 3-substituted 4-phthalazone-1-carboxylic acid is that the 3-substituted 4-phthalazone-1 carboxylic acid is treated with an excess of thionyl chloride in chloroform with boiling, followed by distillation with an excess of thionyl chloride, and the residue an amino alcohol in an organic solvent medium at the boil and isolating the product by known methods, for example, extraction of the base with ether, precipitation with hydrogen chloride and subsequent crystallization and the reaction from the corresponding solvent.

Example 1. A mixture of 26.63 g (0.1 mol} 3-phenyl-4-phthalazone-1-carboxylic acid, 23.8 g of thionyl chloride, 2 g of dimethylformamide and 100 ml of dry chloroform in a flask with a reflux condenser equipped with calcium chloride tube, heated in a glycerin bath at 100 ° C until complete dissolution (0.5-1 hour. The solvent and excess thionyl chloride are evaporated to dryness in a water-jet pump vacuum. The residue is dissolved with 200 ml of dry benzene, cast from the insoluble residue into solution 11.7 g p-diethylaminoethanol B YuOll dry benzene and mix quickly. This jelly mixture is heated under reflux for 1 hour at 100 ° C, the precipitate is filtered, washed with benzene, ether and dried to give 40.1 g of crude substance.After crystallization from 700 ml of absolute alcohol, 30.3 g are obtained (yield 75 ° / o) colorless crystalline hydrochloride salt of 3-phenyl-4-phthalazone-1carboxylic acid diethylaminoethyl ester.

Melting point 221-222 ° C, Rf 0.76.

Found, C1 8.77; 8.53; for C.1H24S11MzOz.

Calculated, o / o: C1 8.82.

Example 2. From 13.31 g (0.05 mol of 3-phenyl-4-phthalazone-1-carboxylic acid, the acid chloride was prepared in the same manner as in Example 1, dissolved in 200 ml of anhydrous benzene and poured with stirring into solution 5, 2 g (0.04 mol} 1-dimethylaminopropan-2-ol in 50 ml of dry benzene.

The mixture is heated at 100 ° C under reflux for 2 hours, the precipitate is filtered off, washed with ether and dried. 17.4 g of crude material is obtained, which is dissolved in 200 ml of water, alkalinized with a saturated solution of sodium carbonate and taken up in ether. The ether extract is dried over anhydrous sodium sulfate, saturated with dry chlorides.

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hydrogen chloride, and the precipitate formed is filtered off. 12.8 g (yield 66%) of a colorless hygroscopic amorphous hydrochloric salt of 1-dimethylamino-2-propyl ester of 3-phenyl-4-phthalazone-1-carboxylic acid are obtained. Melting point after reprecipitation from solution in absolute alcohol with dry ether and drying over phosphorus pentoxide 184-185 ° C. Rt 0.72.

Found, o / „: C1 8.93; 9.75; for CaoHa ClNsO ...

Calculated, o / o: C1 9.14.

Example 3. From 13.31 g (0.05 L) of 3-phenyl-4-phthalazone-1-carboxylic acid and 5.2 g (0.05 mol of y-dimethylaminopropanol are prepared in the same manner as in Example 2, 17.5 After extraction with ether and treating the extract with hydrogen chloride, 16.5 (yield = 85 °) of the colorless hydrochloride salt of Dimethylaminopropyl ester of 3-phenyl-4-phthalazone-1-carboxylic acid is isolated. Melting point after crystallization from absolute alcohol and drying over phosphorus pentoxide 197-198 ° C. Rf-0.67.

Paydeno, o / „: C1 8.59; 8.67; for CsoHasClNeO.

Calculated,%: C1 9,14.

Example 4. From 2.66 g (0.01 mol of 3-phenyl-4-phthalazone-1-carboxylic acid and 1.3 N- (p-hydroxyethyl) -piperidine), 3.25 g of crude reaction product was obtained as described above. extraction of the base with ether and precipitation with hydrogen chloride gave 2.51 (yield: 61 ° / o) of the hydrochloride salt of the p- (N-piperidyl) ethyl ester of 3-phenyl-4-phthalazone-1-carboxylic acid.

T. pl. 240 ° C (with decomposition), Rf 0,82.

Found, o / o: C1 8.44; 8.66; for CsaHoiClNgOs.

Calculated o / o. C1 8.57.

Invention invention

A method for preparing aminoalkyl esters chlorohydrates of 3-substituted 4-phthalazone-1-carboxylic acid, characterized in that the 3-substituted 4-phthalazop-1-carboxylic acid is treated with an excess of thionyl chloride in chloroform at the boiling, followed by distillation of the excess of thionyl chloride, by treatment the residue with an amino alcohol in the medium of an organic solvent at the boil and isolating the product by known methods.