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Process for production of pyridine derive

A kind of derivative and pyridine technology, applied in the field of preparation of pyridine derivatives, can solve the problems of high price, toxicity, low yield and the like

Inactive Publication Date: 2005-05-04
FUJIFILM FINECHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] But, there are more problems in the occasion of mass production, namely 2,5-norbornadiene must be a large amount of surplus more than 10 equivalents relative to the substrate; The reaction time is long; The price is expensive; Causes headaches; and problems with stable supply on an industrial scale
[0007] In addition, a method for obtaining pyridine compounds (Tetrahedron Lett., 59, pp.5171 (1969)) has been reported by 1,2,4-triazine and vinyl acetate, but the yield is low, and it is only suitable for use in 1 , a highly active substrate with alkoxycarbonyl groups at the 3, 5, and 6 positions of 2,4-triazine

Method used

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  • Process for production of pyridine derive
  • Process for production of pyridine derive
  • Process for production of pyridine derive

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0077] As the production method of the above-mentioned carboxylic acid vinyl esters, the direct vinylation method (J.Am.Chem.Soc., 69, pp.2439 (1947); J.Polymer.Sci., 1, pp.207 ( 1951); Trans.Faraday Soc., 49, pp.1108(1953); USPat.2,992,246 (1961); European Polymer J., 4, pp.373(1968)), vinyl exchange method (J.Org. Chem., 25, pp.623 (1960); Makromol. Chem., 73, pp.173 (1964); Makromol. Chem., 29, pp.119 (1959); J. Polymer Sci., 27, pp. 269(1958); Polymer Chemistry, 17, pp.227(1960); J.Sci.Eng.Res.Indian Inst.Technol.Kharagpur, 4, pp.265(1960)), Halcon method (J. Am. Chem. Soc., 81, pp. 2552 (1959)) and the like.

[0078] Carboxylic acid vinyl esters specifically include vinyl butyrate, vinyl caproate, vinyl caprylate, vinyl caprate, vinyl dodecanoate, vinyl myristate, vinyl palmitate, vinyl stearate, Vinyl cyclohexanecarboxylate, vinyl pivalate, vinyl octanoate, vinyl monochloroacetate, divinyl adipate, vinyl methacrylate, vinyl crotonate, vinyl sorbate, vinyl benzoate , v...

Embodiment

[0107] Next, the present invention will be described more specifically in conjunction with examples, but the present invention is not limited thereto. In addition, high performance liquid chromatography (hereinafter abbreviated as "HPLC") was used for evaluation of purity.

[0108] In addition, when "HPLC analysis" is described below, the measurement was performed under the following conditions, and when the conditions were changed, the conditions will be described in detail.

[0109] (Measuring conditions for HPLC analysis)

[0110] Column: YMC-A-312

[0111] Detection UV wavelength: 254nm

[0112] Eluent: acetonitrile / water=25 / 75, containing 0.2% by mass each of acetic acid and triethylamine as a buffer

[0113] Eluent flow rate: 1.0ml / min

Synthetic example 1

[0114] Synthesis example 1 (synthesis of raw material 3-(4-pyridyl)-1,2,4-triazine)

[0115] 200 ml of water, 200.0 g (1.92 mol) of 4-cyanopyridine, and 192.0 g (3.84 mol) of hydrazine monohydrate were charged into a 2000 ml four-necked flask, and reacted at 50° C. for 4 hours under stirring conditions. After confirming the disappearance of the raw material by HPLC analysis, 400 ml of toluene was added, and excess hydrazine monohydrate was distilled off, and this operation was repeated once more. 800 ml of water was added, followed by 278.4 g (1.92 mol) of 40% glyoxal aqueous solution, and the reaction was carried out at an external temperature of 100° C. for 2 hours. After the reaction was completed, it was cooled to 5° C. to obtain 222.4 g of the target product in the form of pale yellow crystals (yield 85.2%).

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Abstract

The present invention provides a method for preparing high-purity pyridine derivatives with high yield, low cost and no pollution problem. A method for producing pyridine derivatives, characterized by reacting a 1,2,4-triazine compound with a vinyl ester compound.

Description

technical field [0001] The invention relates to a preparation method of pyridine derivatives, which can be obtained in the fields of medicines, pesticides, catalyst ligands, silver halide photosensitive materials, liquid crystals, electrophotography and organic electroluminescent elements at low cost, high yield and high purity. Pyridine derivatives that are important intermediates in the production of organic photoreceptors and dyes used in Background technique [0002] Various methods for the preparation of substituted pyridines have been reported. For example, a method of thermally condensing a pyridine compound and an N-oxide of a pyridine compound in the presence of platinum-added Pd-C has been reported (Yakugaku Zasshi, 99(12), pp.1176, 1181(1979)) , but the yield is low. In addition, a cross-linking coupling reaction using a Grignard reaction has also been reported (Japanese Patent Application Laid-Open No. 64-003169), but there is a problem that the iodinated pyrid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/06C07D213/16C07D213/22C07D213/30C07D213/38C07D213/61C07D213/79C07D401/04C07D405/04C07D409/04C07D409/14
CPCC07D213/06C07D213/16C07D213/22C07D213/30C07D213/38C07D213/61C07D213/79C07D401/04C07D405/04C07D409/04C07D409/14
Inventor 新藤太一池内文昭
Owner FUJIFILM FINECHEM
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