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Process for production of 2-pyridylpyridine derivatives

A pyridylpyridine and a technology for a process method are applied in the technical field of producing 2-pyridylpyridine derivatives, and can solve problems such as generation of by-products, environmental pollution and the like

Inactive Publication Date: 2002-06-26
FUJIFILM FINECHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the technology involves a halogenation reaction, it causes environmental pollution problems, and by-products are produced in subsequent steps when the iodine used in the iodination reaction remains
Thus, a purification step must be provided prior to the post-iodination step, which is a disadvantage in large-scale synthesis

Method used

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  • Process for production of 2-pyridylpyridine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Dissolve 4.06 g (0.030 mol) of 4-methyl-2-acetylpyridine and 3.56 g (0.032 mol) of 2-methyl-3-dimethylaminoacrolein in 40 ml of tetrahydrofuran, and add to it 3.63 g (0.032 mol) of potassium tert-butoxide were added and heated at 60° C. for 30 minutes. 23.12 g (0.30 mol) of ammonium acetate and 30 ml of acetic acid were added to the mixed solution, and after making it react at 60° C. for 2 hours, the internal temperature was raised to 105° C. to remove tetrahydrofuran, which was then allowed to react at 105° C. for 2 hours. Hours, after the reaction solution was cooled, 80 ml of 25% NaOH aqueous solution was added thereto, followed by extraction with 4×100 ml of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. Toluene was added to the concentrate for recrystallization, whereby 3.30 g (yield: 59.7%) of a pale yellow powder was obtained. HPLC analysis (column: ODS-80TM; Detection UV: 254nm; Flow rate: 1.0ml / min; Eluen...

Embodiment 2

[0034] 5.14 grams (0.030 moles) of 3-acetyl quinoline and 3.12 grams (0.031 moles) of 3-dimethylaminoacrolein were dissolved in 35 milliliters of tetrahydrofuran, and 3.64 grams (0.032 moles) and tert-butyl potassium alkoxide and heated at 60°C for 10 minutes. Subsequently, 18.50 g (0.24 mol) of ammonium acetate and 14 ml of acetic acid were added, and after reacting at 60°C for 2 hours, the internal temperature was raised to 105°C to remove tetrahydrofuran, followed by reacting at 105°C for 2 hours. After the reaction solution was cooled, 60 mL of 25% aqueous NaOH was added, and the mixture was extracted with 4×100 mL of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The concentrate was distilled under reduced pressure (bp. 165-170° C. / 0.1 Torr) to obtain 2.88 g (yield: 56.0%) of a pale yellow liquid. HPLC analysis (column: ODS-80TM; Detection UV: 264nm; Flow rate: 1.0ml / min; Eluent: acetonitrile / water=82 / 18; Buffer: tr...

Embodiment 3

[0035] Dissolve 2.91 g (0.024 mol) of 4-acetylpyridine and 2.97 g (0.030 mol) of 3-dimethylaminoacrolein in 100 ml of THF, add 2.69 g (0.024 mol) and potassium tert-butoxide, and Heat at 60°C for 10 minutes. Subsequently, 23.12 g (0.30 mol) of ammonium acetate and 60 ml of acetic acid were added, and after reacting at 60° C. for 3.5 hours, THF was removed in an evaporator. Then 100 mL of water and 150 mL of 25% aqueous NaOH were added, and the mixture was extracted with 4 x 100 mL of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from hexane to obtain 1.92 g (yield: 51.2%) of colorless flaky crystals. HPLC analysis (column: ODS-80TM; Detection UV: 264nm; Flow rate: 1.0ml / min; Eluent: acetonitrile / water=50 / 50; Buffer: triethylamine 0.1%, acetic acid 0.1%) shows, The purity of the product is 99.3%, and the melting point is 55.8°C-56.0°C. Comparative example 1

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Abstract

A process for the production of 2-pyridylpyridine derivatives usable as intermediates of drugs or agricultural chemicals, which neither requires any expensive special catalyst or special equipment nor causes environmental pollution and can be carried out even on an industrial scale. This process comprises reacting an acetyl-substituted pyridine derivative with a 3-aminoacrolein compound and reacting the obtained product with ammonia or an ammonium salt.

Description

technical field [0001] The invention provides a process for producing 2-pyridylpyridine derivatives that can be carried out on an industrial scale. The method can continuously obtain high yield and high product purity at low production costs. Said 2- Pyridylpyridine derivatives are important intermediates used in the production of pharmaceuticals, agricultural chemicals, catalyst ligands, organic electroluminescent elements, charge transfer materials, electrophotographic photosensitive materials and dyes. Background technique [0002] As a reaction for synthesizing 2-pyridylpyridine derivatives, the Ullmann reaction of 2-bromopyridine and 4-chloropyridine in nitrobenzene is generally known (Khim.Geol.Nauk., 114(1970)), Use cobalt catalyst reaction (Syhthesis, 600 (1975); Chem.Pharm.Bull., 33, 4755 (1985)), in the presence of Pd catalyst, the coupling reaction between alkyltin derivatives and halogenated pyridines (Tetrahedron Lett ., 33, 2199 (1922)), and the coupling react...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/26C07C223/02C07D213/22C07D213/50C07D241/12C07D401/04
CPCC07D213/22
Inventor 须田博一海原剑
Owner FUJIFILM FINECHEM
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