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Method for preparing enamine ketone compound

A technology of ketone compounds and compounds, which is applied in the preparation of enaminone compounds with two substituents on the nitrogen atom, in the field of preparation of enaminone compounds, to achieve the effects of mild reaction conditions, improved production efficiency, and easy separation and purification

Inactive Publication Date: 2010-07-21
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The purpose of the present invention is to provide a new synthesis method with simple synthesis route, mild reaction conditions and cheap and easy-to-obtain raw materials for the problems faced in the synthesis of existing enaminone compounds

Method used

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  • Method for preparing enamine ketone compound
  • Method for preparing enamine ketone compound

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Preparation of 1-dimethylamino-1-buten-3-one:

[0030] Suspend 4.6g (0.2mol) of sodium metal strips in 100ml of anhydrous diethyl ether, add dropwise a solution consisting of 14.7ml (0.2mol) of acetone and 32ml (0.4mol) of ethyl formate at room temperature, the dropwise addition is completed in about 30 minutes, and continue at room temperature Stir for 5h. Add dropwise 70ml (0.245mol) of dimethylamine hydrochloride aqueous solution with a concentration of 3.5mol / L to the obtained enol sodium salt suspension at room temperature, and the dropwise addition is completed in about 30 minutes, continue stirring at room temperature for 2 hours, and let stand to separate the liquids , the aqueous layer was washed with 3 × 30ml of ether, the organic layers were combined, the organic layer was dried overnight with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and the oil pump vacuum distillation gave 17.5ml of light yellow liquid (101-102°C, 5mmHg), ...

Embodiment 2

[0032] Preparation of 1-dimethylamino-2-methyl-1-buten-3-one

[0033] Suspend 4.6g (0.2mol) of sodium metal strips in 100ml of anhydrous ether, add dropwise a solution consisting of 18ml (0.2mol) of methyl ethyl ketone and 32ml (0.4mol) of ethyl formate at room temperature, the dropwise addition is completed in about 30 minutes, and continue at room temperature Stir for 5h. Add dropwise 70ml (0.245mol) of dimethylamine hydrochloride aqueous solution with a concentration of 3.5mol / L to the obtained enol sodium salt suspension at room temperature, and the dropwise addition is completed in about 30 minutes, continue stirring at room temperature for 2 hours, and let stand to separate the liquids , the aqueous layer was washed with 3 × 30ml of ether, the organic layers were combined, the organic layer was dried overnight with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and the oil pump decompression distillation gave 15ml of light yellow liquid (80-8...

Embodiment 3

[0035] Preparation of 1-dimethylamino-2-methyl-1-hexen-3-one

[0036] Suspend 4.6g (0.2mol) of sodium metal strips in 100ml of anhydrous ether, add dropwise a solution consisting of 21.5ml (0.2mol) of 3-pentanone and 32ml (0.4mol) of ethyl formate at room temperature, and complete the dropwise addition in about 30 minutes , Stirring was continued for 5h at room temperature. Add dropwise 70ml (0.245mol) of dimethylamine hydrochloride aqueous solution with a concentration of 3.5mol / L to the obtained enol sodium salt suspension at room temperature, and the dropwise addition is completed in about 30 minutes, continue stirring at room temperature for 2 hours, and let stand to separate the liquids , the aqueous layer was washed with 3 × 30ml of ether, the organic layers were combined, the organic layer was dried overnight with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and the oil pump decompression distillation gave 24ml of light yellow liquid (102-...

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Abstract

The invention discloses a method for preparing an enamine ketone compound, wherein the enamine ketone compound with two substituents on a nitrogen atom is prepared through an enolate intermediate. A formylation reaction is carried out by using a ketone compound with alpha-methyl or alpha-methylene as a substrate to obtain enolate; and a dehydration-condensation reaction of the enolate and dimethylamine hydrochloride is further carried out to obtain the enamine ketone compound. A reaction formula is as shown in the figure. The raw materials adopted by the method are all ordinary and easily obtained materials, and the method has simple preparation process and mild reaction condition, does not need large expensive equipment and is adaptable to industrialized large-scale production; moreover, the reaction selectivity is high, and the prepared enamine ketone has high yield, is easy to separate and purify and has broad application prospect.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for preparing enaminone compounds. Specifically, it relates to a method for preparing enaminone compounds with two substituents on the nitrogen atom through an enolate intermediate. Background technique [0002] Enaminone compounds refer to α, β-unsaturated ketone compounds substituted with amino groups, which are a kind of multifunctional chemical reaction intermediates with both an electrophilic center with a carbonyl group and a nucleophilic center with an amine group. They have very important applications in the synthesis of nitrogen-containing heterocyclic compounds Tetrahedron, 2003, 59: 8463-8480; J.Chem.Rev., 2004, 104: 2433-2480.; the preparation of metal complexes polyhedron, 2004 , 23:15-21. In addition, some literatures in recent years have also reported the anti-inflammatory and anti-viral physiological activities of enaminones: CN 00816675.7, ...

Claims

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Application Information

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IPC IPC(8): C07C221/00C07C225/14C07C225/16
Inventor 申东升邓爵安
Owner GUANGDONG PHARMA UNIV
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