KR920012034A - 2, 3-피리딘 또는 퀴놀린디카르복실산 및 이들의 산 염의 제조방법 - Google Patents

2, 3-피리딘 또는 퀴놀린디카르복실산 및 이들의 산 염의 제조방법 Download PDF

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KR920012034A
KR920012034A KR1019910023377A KR910023377A KR920012034A KR 920012034 A KR920012034 A KR 920012034A KR 1019910023377 A KR1019910023377 A KR 1019910023377A KR 910023377 A KR910023377 A KR 910023377A KR 920012034 A KR920012034 A KR 920012034A
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acid
quinolinedicarboxylic
pyridine
alkyl
general formula
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KR1019910023377A
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KR100198166B1 (ko
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리이 스트롱 헨리
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알퐁스 아아르 노에
아메리칸 사이아나밋드 캄파니
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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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

내용 없음

Description

2, 3-피리딘 또는 퀴놀린디카르복실산 및 이들의 산 염의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 일반 구조식(Ⅱ) ;
    (상기식에서, R 및 R1은 각각 C1-C6알킬기를 나타내며, X 및 Y는 각각 독립적으로 수소, 할로겐, C1-C6알킬, C1-C4히드록시알킬, C1-C4알콕시알킬, C1-C6알콕시, C1-C4알킬티오페녹시, C1-C4할로알킬, 니트로, 시아노, C1-C4알킬아미노, 디저급알킬아미노, C4-C4알킬설포닐 또는 임의적으로 C1-C4알킬, C1-C4알콕시 또는 할로겐기로 치환된 페닐이며, 및, X 및 Y는 함께 취해져서, XY가 하기 일반 구조식 :
    (상기식에서, L,M,Q 및 Z는 각각 수소, 할로겐, C1-C4알킬 또는 C1-C4알콕시이이다)에 의해 나타나는 고리를 형성할 수 있다)을 갖는 2,3-피리딘 또는 퀴놀린디카르복실산 디에스테르를 가수분해하고, 물 및 3.0미만의 이온화 상수 pKa를 갖는 산의 존재하에서, 약 50℃내지 100℃의 온도에서, 상기 디카르복실산 디에스테르를 가열시키고, 상기 반응 혼합물로부터 물 및 알콜을 분리시키고, 약 20℃ 내지 약 35℃의 온도로 나머지 반응 혼합물을 냉각시키고, 나머지 반응 혼합물을 염기 처리하고, 만약 반응 혼합물이 pH1.3 미만의 pH값을 갖는다면, 상기 혼합물의 PH를 1.3 내지 2.0의 값으로 조정하며, 하기 일반식 구조식(Ⅰ) :
    (상기식에서, X 및 Y는 상기 일반 구조식(Ⅱ)에서 정의된 바와 같다)의 2,3-피리딘 및 퀴놀린디카르복실산을 pH조정된 혼합물로부터 분리시키는 것을 특징으로 하는, 상기 일반 구조식(Ⅰ)를 갖는 2,3-피리딘 또는 퀴놀린디카르복실산의 제조방법.
  2. 제1항에 있어서, 가수분해에서 사용된 산이 황산, 아황산, 염산, 브롬화수소산, 삼불화이세트산, 삼염화아세트산, β-나프탈렌 설폴산, 벤젠 설폰산, P-톨루엔 설폰산, P-에틸벤젠 설폴산, 이염화아세트산 또는 인산이며, 처리된 디에스테르의 몰당 약 3 내지 5몰 당량으로 사용되는 방법.
  3. 제1항에 있어서, 염기가 알킬리 금속 수산화물의 수용액인 방법.
  4. 제1항에 있어서, pH 1.3 내지 pH2.0의 pH값으로 조정된 반응 혼합물을 여과시켜 상기 일반 구조식(Ⅰ)의 2,3-피리딘디카르복실산을 얻는 방법.
  5. 제1항에 있어서, 산이 황산, 염산 또는 브롬화 수소산이며, 염기가 수산화나트륨인 방법.
  6. 제1항에 있어서, 2,3-피리딘 또는 퀴놀린디카르복실산이 5-에틸-2,3-피리딘디카르복실산, 5-메톡시메틸-2,3-피리딘디카르복실산, 2,3-퀴놀린디카르복실산, 5-메틸-2,3-피리딘디카르복실산- 또는 2,3-퀴놀린디카르복실산이며, 산이 황산, 염산 또는 브롬화수소산이며, 염기는 수산화 나트륨인 방법.
  7. 하기 일반 구조식(Ⅱ) :
    (상기식에서, R 및 R1각각 C1-C6알킬기를 나타내며, X 및 Y는 각각 독립적으로 수소, 할로겐, C1-C6알킬, C1-C4히드록시알킬, C1-C4알콕시알킬, C1-C6알콕시, C1-C4알킬티오, 페녹시, C1-C4할로알킬, 니트로, 시아노, C1-C4알킬아미노, 디저급알킬아미노, C4-C4알킬설포닐 또는 임의적으로 C1-C4알킬, C1-C4알콕시 또는 할로겐기로 치환된 페닐이며, 및, X 및 Y는 함께 취해져서, XY가 하기 일반 구조식 :
    (상기식에서, L,M,Q 및 Z는 각각 수소, 할로겐, C1-C4알킬 또는 C1-C4알콕시이이다)에 의해 나타나는 고리를 형성할 수 있다)을 갖는 2,3-피리딘 또는 퀴놀린디카르복실산 디에스테르를 물 및 3.0미만의 pKa를 갖는 산의 존재하에서, 약 50℃내지 110℃의 온도에서, 가수분해시키고, 상기 가열된 혼합물을 약 20℃ 내지 약 40℃의 온도로 냉각시키고, 상기 냉각된 혼합물을, 휘발성 염소화 탄화수소, 에테르 또는 물-불혼화성 알콜을 사용하여 세척하고, 세척된 혼합물에 1,1′-옥시비스[2-메톡시에탄] : 2, 5, 8, 11-테트라옥사도데칸 또는 2, 5, 8, 11, 14-펜타옥사펜타데칸을 첨가하며, 물을 분리시며 산 염으로서 일반 구조식(Ⅰ)의 2, 3-피리딘 또는 퀴놀린디카르복실산을 얻으며, 임의적으로 상기 산 염을 물로 또는 수성 염기내에 분산시켜 일반 구조식(Ⅰ)의 2,3-피리딘 또는 퀴놀린디카르복실산을 얻는 것을 특징으로 하는 상기 일반 구조식(Ⅰ)을 갖는 2,3-피리딘 또는 퀴놀린디카르복실산의 산 염을 제조하는 방법.
  8. 제7항에 있어서, 2,3-피리딘 또는 퀴놀린디카르복실산이 5-메틸-2,3-피리딘디카르복실산, 5-메톡시메틸-2,3-피리딘디카르복실산, 2,3-피리딘디카르복실산, 5-메틸-2,3-피리딘디카르복실산 또는 2,3-퀴놀린디카르복실산인 방법.
  9. 제7항에 있어서, 사용된 산이 염산이고, 디에스테르의 몰당 약 1.5 내지 5몰 당량의 산을 사용하는 방법.
  10. 제7항에 있어서, 휘발성 염소화 탄화수소가 디클로로메탄, 클로로포롬 또는 사염화탄소이며, 에테르는 디에틸 에테르 또는 테트라히드로푸란이며, 및 물-불혼화성 알콜이 n-부탄을, n-헥산을 또는 n-탄올인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019910023377A 1990-12-19 1991-12-18 2,3-피리딘 또는 퀴놀린디카르복실산 및 이들의 산 염의 제조 방법 KR100198166B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/631,594 US5122608A (en) 1990-12-19 1990-12-19 Method for the preparation of substituted and unsubstituted 2,3-pyridine and quinolinedicarboxylic acids
US7/631,594 1990-12-19

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KR920012034A true KR920012034A (ko) 1992-07-25
KR100198166B1 KR100198166B1 (ko) 1999-06-15

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US (1) US5122608A (ko)
EP (1) EP0491140B1 (ko)
JP (1) JPH04295466A (ko)
KR (1) KR100198166B1 (ko)
AT (1) ATE151072T1 (ko)
AU (1) AU637277B2 (ko)
BR (1) BR9105447A (ko)
CA (1) CA2057787A1 (ko)
DE (1) DE69125461T2 (ko)
DK (1) DK0491140T3 (ko)
ES (1) ES2099728T3 (ko)
GR (1) GR3023302T3 (ko)
HU (1) HU208956B (ko)
IE (1) IE914432A1 (ko)
IL (1) IL99882A (ko)
PT (1) PT99816B (ko)
SG (1) SG47574A1 (ko)
TW (1) TW198713B (ko)
ZA (1) ZA919958B (ko)

Families Citing this family (4)

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Publication number Priority date Publication date Assignee Title
US5208342A (en) * 1992-03-30 1993-05-04 Hoechst Celanese Corporation Conversion of pyridine-2,3-dicarboxylic acid esters to cyclic anhydrides
US5284955A (en) * 1992-10-28 1994-02-08 American Cyanamid Company Substituted-2,3-dicarboxypyridinium nitrates
ES2709063T3 (es) * 2016-08-15 2019-04-15 Helmholtz Zentrum Geesthacht Composición inhibidora de la corrosión para magnesio o aleaciones de magnesio
EP3782985A1 (en) 2019-08-19 2021-02-24 BASF Agrochemical Products B.V. Process for manufacturing 5-methoxymethylpyridine-2,3-dicarboxylic acid derivatives

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR880375A (fr) * 1940-07-26 1943-03-24 Ig Farbenindustrie Ag Procédé pour préparer à partir de leurs esters des acides carboxyliques de la série pyridique
GB880592A (en) * 1959-03-16 1961-10-25 Koppers Co Inc Improvements in or relating to pyridine carboxylic acid preparation
US3027380A (en) * 1959-06-10 1962-03-27 Lilly Co Eli Process for preparing 5-fluoronicotinic acid
BE788353A (fr) * 1972-07-26 1973-01-02 Labofina Sa Procede d'oxydation de la quinoleine
US3829432A (en) * 1973-04-02 1974-08-13 Labofina Sa Process for the oxidation of quinoline
US4798619A (en) * 1980-06-02 1989-01-17 American Cyanamid Co. 2-(2-imidazolin-2-yl)-pyridines and quinolines and use of said compounds as herbicidal agents
DE3150005A1 (de) * 1981-12-17 1983-06-23 Rütgerswerke AG, 6000 Frankfurt Verfahren zur herstellung von chinolinsaeure
US4656283A (en) * 1982-05-25 1987-04-07 American Cyanamid Company Alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid
US4460776A (en) * 1982-05-25 1984-07-17 American Cyanamid Company Process for the preparation of 6-substituted-2,3-pyridinedicarboxylic acid diesters
US4608079A (en) * 1983-08-02 1986-08-26 American Cyanamid Company Imidazolidinones, and imidazolidinethiones, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents
DE3345223A1 (de) * 1983-12-14 1985-06-27 Rütgerswerke AG, 6000 Frankfurt Verfahren zur herstellung von chinolinsaeure aus chinolin
US4723011A (en) * 1985-10-28 1988-02-02 American Cyanamid Company Preparation of substituted and disubstituted-pyridine-2,3-dicarboxylate esters
EP0274379B1 (en) * 1987-01-06 1993-06-30 Sugai Chemical Industry Co., Ltd. Process for preparing pyridine-2,3-dicarboxylic acid compounds
US4847405A (en) * 1987-03-19 1989-07-11 American Cyanamid Company Method for the preparation of anilinofumarate [quinoline-2,3- dicarboxylic]
GB8709228D0 (en) * 1987-04-16 1987-05-20 Shell Int Research Preparation of heterocyclic compounds
JPH0625116B2 (ja) * 1987-07-08 1994-04-06 ダイソー株式会社 ピリジン−２，３−ジカルボン酸誘導体の製造法

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DE69125461T2 (de) 1997-07-17
HU914008D0 (en) 1992-03-30
IE914432A1 (en) 1992-07-01
AU8985891A (en) 1992-06-25
ZA919958B (en) 1992-10-28
SG47574A1 (en) 1998-04-17
ES2099728T3 (es) 1997-06-01
US5122608A (en) 1992-06-16
GR3023302T3 (en) 1997-08-29
HUT59670A (en) 1992-06-29
BR9105447A (pt) 1992-08-25
CA2057787A1 (en) 1992-06-20
HU208956B (en) 1994-02-28
AU637277B2 (en) 1993-05-20
ATE151072T1 (de) 1997-04-15
JPH04295466A (ja) 1992-10-20
DK0491140T3 (da) 1997-04-21
PT99816A (pt) 1992-12-31
DE69125461D1 (de) 1997-05-07
IL99882A (en) 1995-05-26
EP0491140B1 (en) 1997-04-02
TW198713B (ko) 1993-01-21
EP0491140A1 (en) 1992-06-24
PT99816B (pt) 1999-05-31
IL99882A0 (en) 1992-08-18
KR100198166B1 (ko) 1999-06-15

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