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Preparation method of 1,8-dinitro-9-fluorenone

A technology of fluorenone and diketone, which is applied in the direction of organic chemistry and the like, achieves the effects of easy availability of preparation raw materials, simple and efficient preparation process, and cheap preparation of raw materials

Inactive Publication Date: 2012-03-21
SUZHOU BEC BIOLOGICAL TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0028] This invention patent uses 2-methoxy-p-phenylenediamine sulfate as raw material, but the total yield of the four-step reaction is 15.3%, which is low

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  • Preparation method of 1,8-dinitro-9-fluorenone

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Embodiment Construction

[0082] A kind of preparation method of 1,8-diaza-9-fluorenone, it comprises the following steps:

[0083] Step 1: Synthesis of 2-methoxy-4-nitroaniline from 2-methoxyaniline;

[0084] Step 2: the 2-methoxy-4-nitroaniline is reduced to generate 2-methoxy-p-phenylenediamine sulfate;

[0085] Step 3: The 2-methoxy-p-phenylenediamine sulfate is synthesized twice for the Skraup quinoline ring to generate 5(6)-methoxy-4,7-phenanthrene;

[0086] Step 4: The 5(6)-methoxy-4,7-phenanthroline is oxidized to generate 4,7-phenanthrene-5,6-dione;

[0087] Step 5: The 4,7-phenanthrene-5,6-dione is condensed in an alkaline aqueous solution to obtain the product DFO, and the total yield of DFO synthesized by five steps is 26.3%.

[0088] Hereinafter, the above steps will be described in detail in conjunction with specific experimental data.

[0089] Step 1: Synthesis of 2-methoxy-4-nitroaniline from 2-methoxyaniline;

[0090] 250ml four-neck flask, equipped with electromagnetic stirrer, re...

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Abstract

The invention discloses a preparation method of 1,8-dinitro-9-fluorenone (DFO). The preparation method of DFO comprises the following steps that 2-methoxy-4-nitroaniline is synthesized from 2-methoxyaniline; the 2-methoxy-4-nitroaniline is reduced into 2-methoxy-p-phenylenediamine sulfate; the 2-methoxy-p-phenylenediamine sulfate undergoes Skraup quinoline synthesis twice to produce 5(6)-methoxy-4,7-naphthisodiazine; the 5(6)-methoxy-4,7-naphthisodiazine undergoes an oxidation reaction to produce 4,7-naphthisodiazine-5,6-diketone; and the 4,7-naphthisodiazine-5,6-diketone is circulated in an alkaline aqueous solution to produce a product DFO, wherein an overall yield of the five DFO synthesis steps is 26.3%. The preparation method of DFO simplifies a preparation process and effectively reduces a production cost. Through the preparation method of DFO, DFO output can satisfy domestic demands on DFO.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of 1,8-diaza-9-fluorenone. Background technique [0002] 1,8-diazafloren-9-fluorenone (1,8-diazafloren-9-one, hereinafter referred to as DFO) is a fluorescence analysis reagent for α-amino acid polypeptides, especially suitable for the detection of sweat fingerprints. The chemical structural formula of the DFO is shown in formula (i). [0003] [0004] The DFO reacts with α-amino acid to generate a red substance showing strong fluorescence, which has strong absorption at 470nm (excitation) and 510nm (emission) respectively, and is used as the analysis and detection means of amino acid and sweat fingerprint. At present, DFO has been widely used by domestic criminal investigation departments as a high-sensitivity sweat fingerprint detection reagent. [0005] For a long time, domestic criminal investigation departments have generally used ninhydrin as a dis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 李文遐
Owner SUZHOU BEC BIOLOGICAL TECH
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