Synthetic method for 2-amino-1,10-phenanthroline

A technology of o-phenanthroline and its synthesis method, which is applied in the field of preparation of 2-amino-1,10-phenanthroline, and can solve the problems of less access, less performance and application research, etc.

Active Publication Date: 2015-12-23
杭州晟大应用材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] 2-Amino-1,10-phenanthroline is an important 2-position derivative in 1,10-phenanthroline derivatives, and the main synthesis method is through 2-halo-1,10-phenanthroline It is obtained by ammoniation reaction. Due to the lack of access, there are relatively few studies on the properties and applications of 2-amino-1,10-phenanthroline reported in the literature.

Method used

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  • Synthetic method for 2-amino-1,10-phenanthroline

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Add 20mL toluene, 1.96g (10mmol) 1,10-phenanthrolin-2-one, 9.53g (50mmol) p-toluenesulfonyl chloride, 5g (50mmol) 1-methylpiperidine in the flask, stir, Heat to 112°C and reflux for 12 hours (TLC tracking), cool slightly, add 20 mL of concentrated ammonia water, heat and reflux for 4 hours, cool, add 20 mL of water, separate layers, extract the aqueous layer with 20 mL of chloroform, combine the organic layers, and concentrate to dryness. The residue was purified by silica gel chromatography (the mobile phase was ethyl acetate) to obtain 1.53 g of white solid, yield 78%, Mp 187-189°C.

Embodiment 2

[0011] Add 20mL xylene, 1.96g (10mmol) 1,10-phenanthrolin-2-one, 11.4g (100mmol) methanesulfonyl chloride, 10.1g (100mmol) triethylamine into the flask, stir and heat to 70°C React for 6h (TLC tracking), cool slightly, add 20mL of concentrated ammonia water, heat to reflux for 6h, cool, add 40mL of water, separate layers, extract the aqueous layer with 20mL of chloroform, combine the organic layers, concentrate to dryness, and wash the residue with silica gel layer Purification by column analysis (mobile phase is ethyl acetate) to obtain 0.22 g of white solid, yield 11%, Mp 187-189°C.

Embodiment 3

[0013] Add 20mL dimethyl sulfoxide, 1.96g (10mmol) 1,10-phenanthrolin-2-one, 9.53g (50mmol) benzylsulfonyl chloride, 5.4g (50mmol) sodium carbonate in the flask, stir and heat React at 90°C for 6h (TLC tracking), cool slightly, add 20mL of concentrated ammonia water, heat to reflux for 4h, concentrate the solvent under reduced pressure, add 20mL of water to the residue, extract the aqueous layer with 20mL*2 chloroform, concentrate the extract to dryness, and leave The compound was purified by silica gel column chromatography (mobile phase was ethyl acetate) to obtain 1.0 g of white solid, yield 51%, Mp 187~189°C.

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Abstract

The invention provides a synthetic method for 2-amino-1,10-phenanthroline. The method comprises the following steps: in an aprotic solvent, subjecting 1,10-phenanthroline-2-one and alkyl sulfonyl chloride to sulfonylation in the presence of alkali so as to obtain 1,10-phenanthroline-2-sulfonate; and subjecting the obtained 1,10-phenanthroline-2-sulfonate without separation to heating reaction with ammonia water and then carrying out separating so as to obtain 2-amino-1,10-phenanthroline. The aprotic solvent used in the method may be toluene, xylene, dimethyl sulfoxide, diethylene glycol dimethyl ether or the like, the alkali may be triethylamine, 1-methyl piperidine, pyridine, sodium carbonate or the like, and the alkyl sulfonyl chloride may be p-methylbenzenesulfonyl chloride, benzenesulfonyl chloride, benzylsulfonyl chloride, methylsulfonyl chloride or the like, preferably, p-methylbenzenesulfonyl chloride.

Description

technical field [0001] The invention relates to a preparation method of 2-amino-1,10-phenanthroline. Background technique [0002] 1,10-phenanthroline is a classic ligand. 1,10-phenanthroline and its derivatives play an important role in coordination chemistry. As good metal ligands, they have antibacterial and antitumor , catalytic reactions, supramolecular chemistry, DNA probes, molecular switches, etc. are widely used. Structural modification on the basis of 1,10-phenanthroline is an important way to obtain 1,10-phenanthroline derivatives. The derivatives obtained by this method are mainly concentrated in 2,9-, 3,8-, 5,6-position, of which the 5,6-position has the most derivatives. [0003] 2-Amino-1,10-phenanthroline is an important 2-position derivative in 1,10-phenanthroline derivatives, and the main synthesis method is through 2-halo-1,10-phenanthroline It can be obtained by ammoniation reaction. Due to the lack of access, there are relatively few studies on the pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 施晓婕郭海昌雷海芳姜霞丽
Owner 杭州晟大应用材料有限公司
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