KR910014351A - 치환된 2-클로로피리딘의 제조방법 - Google Patents

치환된 2-클로로피리딘의 제조방법 Download PDF

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KR910014351A
KR910014351A KR1019910000586A KR910000586A KR910014351A KR 910014351 A KR910014351 A KR 910014351A KR 1019910000586 A KR1019910000586 A KR 1019910000586A KR 910000586 A KR910000586 A KR 910000586A KR 910014351 A KR910014351 A KR 910014351A
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South Korea
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chloride
reacted
process according
alkyl
chlorine
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KR1019910000586A
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KR100198041B1 (ko
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카우프만 디이터
옐리히 클라우스
브라덴 루돌프
로젠 빈프리드
Original Assignee
클라우스 댄너, 롤프 브라운
바이엘 아크티엔게젤샤프트
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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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • 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
    • C07D213/61—Halogen atoms or nitro radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

내용 없음

Description

치환된 2-클로로피리딘의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 일반식(Ⅱ)의 피리딘-1-옥사이드를 불활성 유기용매 및 산 수용체 존재하에 -20내지 200℃에서 방향족카보닐 클로라이드와 반응시킨 다음, 70 내지 160℃에서 필요하다면 활성화제 존재하에 포스겐 또는 티오닐 클로라이드와 임의로 반응시키고, 이렇게 하여 수득한 생성물을 임의로 추가 치환시킴을 특징으로 하여, 일반식(Ⅰ)의 치환된 2-클로로피리딘 유도체를 제조하는 방법.
    상기식에서, R1은 수소, 불소, 염소, 시아노, 카브알콕시(C1-C4) 또는(여기에서, R5와 R6는 동일하거나 상이하고 알킬(C1-C4)을 나타낸다)을 나타내고, R2는 수소, 불소, 염소, 알킬(C1-C4), 할로게노알킬(C1-C|4), 시아노알킬(C1-C4), 알콕시(C1-C4)알킬(C1-C4), 디알킬아미노(C|1-C4)알킬(C1-C4), 아실(C1-C4)-아세탈, 카브알콕시(C1-C4) 또는(여기에서, R5와 R6는 동일하거나 상이하고 알킬(C1-C4)을 나타낸다)을 나타내거나 R1과 R2과 함께 2가 그룹 -CH=CH-CH=CH-을 나타내며, R3은 수소, 염소, 카브알콕시(C1-C4) 또는(여기에서, R6와 R7는 동일하거나 상이하고 알킬(C1-C4)을 나타낸다)을 나타내며, R4는 수소, 불소, 염소 또는 시아노를 나타내거나 R3와 R4가 함께 2가 그룹 -CH=CH-CH-CH-를 나타낸다.
  2. 제1항에 있어서, 반응의 방향족 카보닐 클로라이드로서 벤조일 클로라이드, 모노클로로벤조일 클로라이드, 디클로로벤조일 클로라이드, 모노메틸벤조일 클로라이드, 모노클로로메틸벤조일 클로라이드, 디메틸벤조일 클로라이드, 모노메톡시벤조일 클로라이드, 모노니트로벤조일 클로라이드, 프탈로일 클로라이드, 디클로로프탈리드, 모노 클로로프탈로일 클로라이드, 디클로로프탈로일 클로라이드, 모노니트로프탈로일 클로라이드 및 나프탈렌카보닐 클로라이드가 사용되는 방법.
  3. 제1항 또는 2항에 있어서, 산 수용체로서 트리알킬아민, 디알킬-사이클로알킬아민 및 다알킬아르알킬아민을 포함하는 계열의 염기성 유기질소 화합물이 사용되는 방법.
  4. 제1항 내지 3항중 어느 한 항에 있어서, 산 수용체로서 트리에틸아민이 사용되는 방법.
  5. 제1항 내지 4항중 어느 한 항에 있어서, 활성화제로서 포름아미드를 포함하는 계열의 화합물이 사용되는 방법.
  6. 제1항 내지 5항중 어느 한 항에 있어서, 불활성 유기용매로서 메틸렌 클로라이드, 에틸렌 클로라이드, 1,1,2-트리클로로에탄, 1,2-디클로로프로판, 1,2,3-트리클로로프로판, 클로로포름 또는 클로로벤젠이 사용되는 방법.
  7. 제1항 내지 6항중 어느 한 항에 있어서, 방향족산 클로라이드와 0내지 160℃에서 반응시키고 필요하다면 계속해서 포스겐 또는 티오닐 클로라이드와 70내지 160℃에서 반응시키는 방법.
  8. 제1항 내지 7항중 어느 한 항에 있어서, 방향족 카보닐 클로라이드 1내지 10mol을 일반식(Ⅱ)의 치환된 피리딘-1-옥사이드 1mol과 아민 1내지 10mol의 용액에 적가하고 필요하다면 포름아미드를 계속해서 가하고 포스겐 2내지 5mol을 도입시키거나 티오닐 클로라이드를 적가한 다음 반응 혼합물을 수 시간동안 교반하는 방법.
  9. 제1항 내지 8항중 어느 한 항에 있어서, 반응에서 형성된 반응 혼합물을 증기 증류시키는 방법.
  10. 제1항 내지 9항중 어느 한 항에 있어서, 2-클로로-5-메틸피리딘을 제조하기 위하여, 3-메틸-피리딘-1-옥사이드를 산 수용체로서 트리에틸아민의 첨가하에 메틸렌 클로라이드, 에틸렌 클로라이드, 1,2-디클로로프로판, 1,2,3-트리클로로프로판 또는 클로로벤젠중에서 벤조일 클로라이드 또는 프탈로일 클로라이드와 반응시키고 클로로벤젠중에서 수행할 경우 포름아미드를 가한 후에 포스겐을 계속해서 도입시키거나 티오닐 클로라이드를 적가하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019910000586A 1990-01-18 1991-01-16 치환된 2-클로로피리딘의 제조방법 KR100198041B1 (ko)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE4001248 1990-01-18
DE4020055.8 1990-06-23
DE4020055A DE4020055A1 (de) 1990-01-18 1990-06-23 Verfahren zur herstellung von substituierten 2-chlor-pyridinen
DE4001248.4 1990-06-23
DE40200558 1990-06-23

Publications (2)

Publication Number Publication Date
KR910014351A true KR910014351A (ko) 1991-08-31
KR100198041B1 KR100198041B1 (ko) 1999-06-15

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Application Number Title Priority Date Filing Date
KR1019910000586A KR100198041B1 (ko) 1990-01-18 1991-01-16 치환된 2-클로로피리딘의 제조방법

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Country Link
US (1) US5334724A (ko)
EP (1) EP0438691B1 (ko)
JP (1) JP3100168B2 (ko)
KR (1) KR100198041B1 (ko)
DE (2) DE4020055A1 (ko)
HU (1) HU207994B (ko)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4020053A1 (de) * 1990-01-31 1991-08-01 Bayer Ag Verfahren zur herstellung von 2-chlor-5-methyl-pyridin
DE4311247A1 (de) * 1993-04-06 1994-10-13 Bayer Ag Verfahren zur Herstellung von 2-Halogen-pyridin-derivaten
US5502194A (en) * 1992-02-19 1996-03-26 Bayer Aktiengesellschaft Process for the preparation of 2-halogeno-pyridine derivatives
DE4212595A1 (de) * 1992-02-19 1993-08-26 Bayer Ag Verfahren zur herstellung von 2-chlor-5-methyl-pyridin
DK0798296T3 (da) * 1996-03-21 2004-04-05 Lonza Ag Fremgangsmåde til fremstilling af arylamider af heteroaromatiske carboxylsyrer
SK283920B6 (sk) 1996-03-28 2004-05-04 Lonza Ag Spôsob výroby arylamidov heteroaromatických karboxylových kyselín
US5900484A (en) * 1996-09-18 1999-05-04 Lonza Ag Process for the preparation of arylamides of heteroaromatic carboxylic acids
DK0806415T3 (da) * 1996-05-09 2000-06-05 Lonza Ag Fremgangsmåde til fremstilling af arylamider af heteroaromatiske carboxylsyrer
CA2209392C (en) * 1996-07-23 2007-02-20 Yves Bessard Process for preparing pyridinecarboxylic esters
US6169183B1 (en) 1996-07-23 2001-01-02 Lonza, Ltd. Process for preparing pyridinecarboxylic esters
KR100543694B1 (ko) * 1999-01-19 2006-01-23 주식회사 코오롱 2-클로로피리딘의 제조방법
CN101260076B (zh) * 2007-03-08 2012-04-11 南京红太阳生物化学有限责任公司 2-氯-5-甲基吡啶的制备方法
CN102219732B (zh) * 2011-04-22 2013-04-17 安徽国星生物化学有限公司 一种2-氯-5-甲基吡啶化合物的制备方法
WO2022099692A1 (zh) * 2020-11-16 2022-05-19 单县欣润化工有限公司 一种2-氯-5-三氟甲基吡啶合成方法及系统

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1200304B (de) * 1963-01-26 1965-09-09 Leuna Werke Veb Verfahren zur Herstellung von Chlorpyridinen und ihren alkylsubstituierten Homologen
US4628096A (en) * 1983-05-20 1986-12-09 Ici Americas Inc. Preparation of 2-halo-5-methylpyridines from 4-methyl-4-pentene derivatives
DE3839332A1 (de) * 1988-11-22 1990-05-23 Bayer Ag Verfahren zur herstellung von substituierten 2-chlorpyridinen
DE4020053A1 (de) * 1990-01-31 1991-08-01 Bayer Ag Verfahren zur herstellung von 2-chlor-5-methyl-pyridin
DE4020052A1 (de) * 1990-06-23 1992-01-02 Bayer Ag Verfahren zur herstellung von 2-chlor-5-methyl-pyridin

Also Published As

Publication number Publication date
HU910151D0 (en) 1991-08-28
JPH04210964A (ja) 1992-08-03
US5334724A (en) 1994-08-02
HUT56825A (en) 1991-10-28
KR100198041B1 (ko) 1999-06-15
DE59004613D1 (de) 1994-03-24
EP0438691B1 (de) 1994-02-16
EP0438691A1 (de) 1991-07-31
DE4020055A1 (de) 1991-07-25
HU207994B (en) 1993-07-28
JP3100168B2 (ja) 2000-10-16

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