KR940003935A - Method for preparing pyridine derivative - Google Patents

Method for preparing pyridine derivative Download PDF

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Publication number
KR940003935A
KR940003935A KR1019920014041A KR920014041A KR940003935A KR 940003935 A KR940003935 A KR 940003935A KR 1019920014041 A KR1019920014041 A KR 1019920014041A KR 920014041 A KR920014041 A KR 920014041A KR 940003935 A KR940003935 A KR 940003935A
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South Korea
Prior art keywords
formula
derivative
compound
benzyloxyacetyl
reacting
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KR1019920014041A
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Korean (ko)
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KR960005828B1 (en
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김상호
박호진
이강노
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하기주
주식회사 코오롱
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Abstract

본 발명은 위산분비 억제특성을 갖는 벤즈이미다졸 유도체의 제조에 사용되는 아래 구조식(Ⅰ)의 피리딘 유동체의 제조방법에 관한 것이다.The present invention relates to a method for preparing a pyridine fluid of formula (I) used for the preparation of benzimidazole derivatives having gastric acid secretion inhibitory properties.

본 발명은 아래 구조식(Ⅳ)의 펜텐온 유도체를 아래 구조식(Ⅴ)의 벤질옥시아세틸 라디칼과 촉매 하에서 반응시켜 아래 구조식(Ⅵ) 및 (Ⅶ)의 화합물을 제조한 다음, 알코올 용매 하에서 암모니아 유도체와 반응시켜서 구조식(Ⅷ)의 피리딘온 유도체를 합성하고, 이를염소화제와 반응시켜 구조식(Ⅸ)의 클로로피리딘 유도체를 제조하고, 금속 알콕시드와 반응시켜 구조식(Ⅹ)의 메톡시드 피리딘 유도체를 제조한 후, 수소화반응을 시켜 3, 5-디메틸-4-메톡시-2-히드록시메틸피리딘(Ⅰ)을 제조하는 방법이다.The present invention is prepared by reacting a pentenone derivative of formula (IV) below with a benzyloxyacetyl radical of formula (V) under a catalyst to produce a compound of formulas (VI) and (iii), followed by ammonia derivatives in an alcohol solvent. By reacting to synthesize a pyridinone derivative of formula (VII), reacting it with a chlorinating agent to produce a chloropyridine derivative of formula (IV), and reacting with a metal alkoxide to prepare a methoxide pyridine derivative of formula (VII) Then, hydrogenation reaction is carried out to produce 3,5-dimethyl-4-methoxy-2-hydroxymethylpyridine (I).

식중 X는 Cl, Br, I 또는이다.Wherein X is Cl, Br, I or to be.

본 발명은, 종래기술에 있어서의 공정이 길고 복잡하며 전체 수율이 낮고 발암성의 중간체가 형성되며 원료가 고가인 단점을 극복하는 새로운 제조공정으로, 수율이 향상되고 피리딘환을 직접 형성시키며 반응성이 매우 우수한 경제적인 방법이다.The present invention is a new manufacturing process that overcomes the disadvantages of the long and complex process in the prior art, the overall yield is low, the carcinogenic intermediate is formed and the raw material is expensive, the yield is improved, and the pyridine ring is directly formed and the reactivity is very high. It is an excellent economic way.

Description

피리딘 유도체의 제조방법Method for preparing pyridine derivative

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (9)

아래 구조식 (I)로 나타낸 히드록시메틸 피리딘 유도체를 제조하는데 있어서, 아래 구조식 (Ⅳ)의 펜텐온 유도체로부터 아래 구조식(Ⅷ)의 피리딘온 유도테를 합성하여, 이를 염소화제와 반응시켜 아래 구조식(Ⅸ)의 클로로피리딘 유도체를 제조하고, 금속 알콕시드와 반응시켜 아래 구식(Ⅹ)의 메톡시드 피리딘 유도체를 제조한 후 수소화반응을 시켜, 3, 5-디 메틸-4-메톡시 -2-히드록시 메틸피리딘 (I)을 제조하는 것을 특징으로 하는 제조 방법.In preparing the hydroxymethyl pyridine derivative represented by the following structural formula (I), a pyridinone derivative of the following structural formula (VII) is synthesized from the pentenone derivative of the following structural formula (IV), and reacted with a chlorinating agent to give the following structural formula ( Chloropyridine derivative of (iii) is prepared, and reacted with metal alkoxide to produce methoxide pyridine derivative of the following old formula, and then hydrogenated to produce 3, 5-dimethyl-4-methoxy-2-hydride. A process for producing hydroxy methylpyridine (I). 제1항에 있어서, 구조식(Ⅷ)의 화합물의 제조는 구조식(Ⅳ)의 화합물을 아래 구조식(V)의 벤질옥시아세틸 라디칼과 촉매 하에서 반응시켜 아래 구조식(Ⅵ) 및 Ⅶ)의 화합물을 제조한 다음, 알코올 용매 하에서 암모니아 유도체와 반응시킴을 특징으로 하는 제조방법.The method of claim 1, wherein the compound of formula (VII) is prepared by reacting the compound of formula (IV) with a benzyloxyacetyl radical of formula (V) under a catalyst to prepare a compound of formulas (VI) and (iii). Next, the production method characterized in that the reaction with an ammonia derivative in an alcohol solvent. 식중 X는 Cl, Br, I 또는이다.Wherein X is Cl, Br, I or to be. 제1항에 있어서 금속 알콕시드가 나트륨 메톡시드 또는 칼륨 메톡시드임을 특징으로 하는 구조식 (I)의 화합물의 제조방법.A process for preparing a compound of formula (I) according to claim 1, wherein the metal alkoxide is sodium methoxide or potassium methoxide. 제1항에 있어서, 염소화제로 Pocl₃ 또는 PCl5를 사용함을 특징으로 하는 제조방법.The method of claim 1, wherein Pocl 3 or PCl 5 is used as the chlorinating agent. 제1항에 있어서, 수소화반응은 Pd/C을 촉매로 사용하여 1-20kg/㎠의 수소압력에서 실시하는 것을 특징으로 하는 제조방법.The method according to claim 1, wherein the hydrogenation reaction is carried out at a hydrogen pressure of 1-20 kg / cm 2 using Pd / C as a catalyst. 제2항에 있어서, 암모니아 유도체와의 반응은 상압에서 암모니움 히드록시와 반응시키거나 5-10kg/㎠의 암모니아(NH₃) 압력 하에서 반응시키는 것을 특징으로 하는 제조방법.The method according to claim 2, wherein the reaction with the ammonia derivative is reacted with ammonium hydroxy at normal pressure or under ammonia (NH₃) pressure of 5-10 kg / cm 2. 제2항에 있어서, 벤질옥시아세틸 라디칼로는 벤질옥시아세틸 클로리드, 벤질옥시아세틸 브로미드 또는 벤질옥시아세틸 무수물인 것을 특징으로 하는 제조방법.3. The process according to claim 2, wherein the benzyloxyacetyl radical is benzyloxyacetyl chloride, benzyloxyacetyl bromide or benzyloxyacetyl anhydride. 제2항에 있어서, 촉매가 리튬 비스(트리메틸실릴) 아미드, 보론 트리플로리드 또는 징크 클로리드임을 특징으로 하는 구조식 (I)의 화합물의 제조방법.The process for preparing the compound of formula (I) according to claim 2, wherein the catalyst is lithium bis (trimethylsilyl) amide, boron trifluoride or zinc chloride. 제2항에 있어서, 알코올이 메탄올 또는 에탄올임을 특징으로 하는 구조식 (I) 화합물의 제조방법.The process for preparing the compound of formula (I) according to claim 2, wherein the alcohol is methanol or ethanol. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019920014041A 1992-08-05 1992-08-05 Process for preparation of pyridine derivatives KR960005828B1 (en)

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KR960005828B1 KR960005828B1 (en) 1996-05-01

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE45415E1 (en) * 2002-02-22 2015-03-17 Oxygenator Water Technologies, Inc. Flow-through oxygenator

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE45415E1 (en) * 2002-02-22 2015-03-17 Oxygenator Water Technologies, Inc. Flow-through oxygenator

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