KR920012034A - 2, 3-피리딘 또는 퀴놀린디카르복실산 및 이들의 산 염의 제조방법 - Google Patents
2, 3-피리딘 또는 퀴놀린디카르복실산 및 이들의 산 염의 제조방법 Download PDFInfo
- Publication number
- 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
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- quinolinedicarboxylic
- pyridine
- alkyl
- general formula
- Prior art date
Links
Classifications
-
- 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
Landscapes
- 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
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 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.
- 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.
- 제1항에 있어서, 염기가 알킬리 금속 수산화물의 수용액인 방법.
- 제1항에 있어서, pH 1.3 내지 pH2.0의 pH값으로 조정된 반응 혼합물을 여과시켜 상기 일반 구조식(Ⅰ)의 2,3-피리딘디카르복실산을 얻는 방법.
- 제1항에 있어서, 산이 황산, 염산 또는 브롬화 수소산이며, 염기가 수산화나트륨인 방법.
- 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.
- 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.
- 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.
- 제7항에 있어서, 사용된 산이 염산이고, 디에스테르의 몰당 약 1.5 내지 5몰 당량의 산을 사용하는 방법.
- 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.
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 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR920012034A true KR920012034A (ko) | 1992-07-25 |
KR100198166B1 KR100198166B1 (ko) | 1999-06-15 |
Family
ID=24531896
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019910023377A KR100198166B1 (ko) | 1990-12-19 | 1991-12-18 | 2,3-피리딘 또는 퀴놀린디카르복실산 및 이들의 산 염의 제조 방법 |
Country Status (19)
Country | Link |
---|---|
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)
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)
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 |
-
1990
- 1990-12-19 US US07/631,594 patent/US5122608A/en not_active Expired - Lifetime
-
1991
- 1991-10-24 AT AT91118108T patent/ATE151072T1/de not_active IP Right Cessation
- 1991-10-24 SG SG1996002900A patent/SG47574A1/en unknown
- 1991-10-24 ES ES91118108T patent/ES2099728T3/es not_active Expired - Lifetime
- 1991-10-24 DK DK91118108.9T patent/DK0491140T3/da active
- 1991-10-24 DE DE69125461T patent/DE69125461T2/de not_active Expired - Fee Related
- 1991-10-24 EP EP91118108A patent/EP0491140B1/en not_active Expired - Lifetime
- 1991-10-29 IL IL9988291A patent/IL99882A/en not_active IP Right Cessation
- 1991-11-05 TW TW080108702A patent/TW198713B/zh active
- 1991-12-13 BR BR919105447A patent/BR9105447A/pt not_active IP Right Cessation
- 1991-12-16 PT PT99816A patent/PT99816B/pt not_active IP Right Cessation
- 1991-12-16 JP JP3352728A patent/JPH04295466A/ja active Pending
- 1991-12-17 CA CA002057787A patent/CA2057787A1/en not_active Abandoned
- 1991-12-18 HU HU914008A patent/HU208956B/hu not_active IP Right Cessation
- 1991-12-18 ZA ZA919958A patent/ZA919958B/xx unknown
- 1991-12-18 KR KR1019910023377A patent/KR100198166B1/ko not_active IP Right Cessation
- 1991-12-18 IE IE443291A patent/IE914432A1/en not_active IP Right Cessation
- 1991-12-18 AU AU89858/91A patent/AU637277B2/en not_active Ceased
-
1997
- 1997-05-02 GR GR960403250T patent/GR3023302T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
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 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR870003989A (ko) | 치환 및 이치환 피리딘-2,3-디카르복실레이트의 제조방법과 치환된 니코티네이트의 제조방법 | |
JP3688295B2 (ja) | 4,6−ジクロロピリミジンの製造方法 | |
KR840000508A (ko) | 4-아닐리노피리미딘 유도체의 제조방법 | |
KR830007638A (ko) | 2-구아니디노-4-헤테로아릴티아졸의 제조방법 | |
KR100215702B1 (ko) | 클로로말레이트 또는 클로로푸마레이트 또는 이들의 혼합물로부터 치환 및 비치환 - 2,3 - 피리딘디카르복실레이트의 제조방법 및 이로써 얻어진 피리딘디카르복실레이트 화합물 | |
AR241593A1 (es) | Procedimiento para preparar derivados de acido quinolin-3-carboxilico. | |
KR920012034A (ko) | 2, 3-피리딘 또는 퀴놀린디카르복실산 및 이들의 산 염의 제조방법 | |
KR840006009A (ko) | 티에노 피리미딘 유도체 및 이의 산부가염의 제조방법 | |
KR850002459A (ko) | 디히드록시벤즈아미드 유도체 및 그 제조방법 | |
KR920014781A (ko) | N-플루오로피리디늄 염의 제조방법 | |
KR940018368A (ko) | 알킬 2-알킬-4-플루오로메틸티아졸카르복실레이트의 제조방법 | |
US3414620A (en) | Multifunctional amine compounds and methods for their preparation | |
KR840001968A (ko) | 4-페닐퀴나졸린 유도체의 제조방법 | |
KR930010036A (ko) | 2-아미노-6-할로게노푸린의 제조방법 및 합성 중간체 | |
KR860008115A (ko) | 알파-나프틸프로피온산의 라세미 혼합물의 광학적 분할방법 | |
KR860001073A (ko) | 이미다졸린의 제조방법 | |
US3900476A (en) | 2(2'-pyrimidylamino)quinazolines and their preparation | |
KR830007510A (ko) | 심장질환 치료제의 제조방법 | |
KR940002230A (ko) | 2-치환된-5-클로로이미다졸-4-카보알데히드의 제조방법 | |
KR890014487A (ko) | 치환-피리딘-2,3-디카르복실산을 생성시키기 위한 치환-8-히드록시퀴놀린의 연속적 산화 방법 | |
KR830007647A (ko) | 벤조헤테로사이클릭 화합물의 제조방법 | |
KR870003078A (ko) | N-설파밀-3-(2-구아니디노-티아졸-4-일-메틸티오)프로피온아미딘의 제조방법 | |
CA1038870A (en) | Pyrimidine derivatives | |
US3892760A (en) | Bis-(2-pyridyl-1-oxide) disulfide | |
US4264770A (en) | Process for preparing 1,4-bis-piperonylpiperazine and similar compounds |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
LAPS | Lapse due to unpaid annual fee |