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Process for production of pyridine derivs.

A derivative, pyridine technology, applied in the field of preparation of pyridine derivatives, can solve the problems of toxicity, long reaction time, low yield, etc.

Inactive Publication Date: 2003-03-12
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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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0067] 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.

[0068] 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 1

[0101] Next, 45 ml of diisopropylbenzene, 25.0 g (0.158 mol) of 3-(4-pyridyl)-1,2,4-triazine synthesized in Synthesis Example 1, and n-decyl 60.1 g (0.316 mol) of vinyl acid ester was reacted at 210° C. for 2 hours under stirring conditions. After confirming the disappearance of the raw material by HPLC analysis, it was diluted with 100 ml of toluene, adjusted to acidity with 180 ml of 1 mol / l hydrochloric acid, and separated. The obtained aqueous layer was washed with 90 ml of toluene, and this operation was repeated once more. The aqueous layer was made basic with 50 ml of a 9 mol / l sodium hydroxide aqueous solution, and extracted with 120 ml of toluene. The solvent was distilled off under reduced pressure, and crystallization was performed with hexane to obtain 22.4 g of the target product as light yellow crystals (90.7% yield). As a result of HPLC analysis, the purity was 99.3%. The melting point is 60-62°C. Embodiment 2~7

Embodiment 2～7

[0102] In Example 1, except that vinyl n-decanoate was replaced with vinyl carboxylate shown in Table 1 below, the operation was carried out in the same manner as in Example 1 to synthesize 2,4'-dipyridyl (A-1), Yield and purity by HPLC were evaluated. Comparative example 1~2

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Abstract

A process for producing high-purity pyridine derivatives in high yield at low cost without environmental pollution, 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 Applications(China)
IPC IPC(8): C07D213/06C07D213/16C07D213/22C07D213/30C07D213/38C07D213/61C07D213/79C07D401/04C07D405/04C07D409/04C07D409/14
CPCC07D213/30C07D213/16C07D409/04C07D213/79C07D213/38C07D405/04C07D409/14C07D213/61C07D213/06C07D213/22C07D401/04
Inventor 新藤太一池内文昭
Owner FUJIFILM FINECHEM
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