KR850002254A - 4-퀴놀리논류의 제법 - Google Patents
4-퀴놀리논류의 제법 Download PDFInfo
- Publication number
- KR850002254A KR850002254A KR1019840005764A KR840005764A KR850002254A KR 850002254 A KR850002254 A KR 850002254A KR 1019840005764 A KR1019840005764 A KR 1019840005764A KR 840005764 A KR840005764 A KR 840005764A KR 850002254 A KR850002254 A KR 850002254A
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- formula
- chloride
- product
- phosgene
- Prior art date
Links
- HETSDWRDICBRSQ-UHFFFAOYSA-N 3h-quinolin-4-one Chemical class C1=CC=C2C(=O)CC=NC2=C1 HETSDWRDICBRSQ-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims 7
- BUWPZNOVIHAWHW-UHFFFAOYSA-N 2,3-dihydro-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)CCNC2=C1 BUWPZNOVIHAWHW-UHFFFAOYSA-N 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 239000002841 Lewis acid Substances 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 150000007517 lewis acids Chemical class 0.000 claims 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- AQKKRXMVSOXABZ-UHFFFAOYSA-N 3-anilinopropanoic acid Chemical compound OC(=O)CCNC1=CC=CC=C1 AQKKRXMVSOXABZ-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims 1
- QKNALXSEDPJVFW-UHFFFAOYSA-J [Sn].[Sn](Cl)(Cl)(Cl)Cl Chemical compound [Sn].[Sn](Cl)(Cl)(Cl)Cl QKNALXSEDPJVFW-UHFFFAOYSA-J 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229920000137 polyphosphoric acid Polymers 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 229950011008 tetrachloroethylene Drugs 0.000 claims 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims 1
Classifications
-
- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Quinoline Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- 하기구조식(Ⅱ)의 3－아닐리노프로피온산을 포스겐으로 처리하여 하기구조식(Ⅲ)의 생성물을 생성한 다음 상기 생성물을 디멜틸포름아미드 존재하에 포스겐과 반응시켜 하기구조식(Ⅳ)의 산염화물을 생성하고 이것을 적당한 용매중에서 루이스산으로 처리하거나 강산으로 처리하여 하기구조식(Ⅴ)의 생성물을 얻고 이것을 무기염기존재하에 가수분해시켜 1,2,3,4－테트라하이드로－4－퀴놀리논을 생성시키는 것으로 구성된 하기구조식(Ⅰ)의 1,2,3,4－테트라하이드로－4－퀴놀리논을 제조하는 방법.상기식들에서, R은 수소원자, 할로겐원자, C1-4직쇄 또는 분지쇄 알킬라디칼 C1-4직쇄 또는 분지쇄 알콕시라디칼을 나타내며, R1은 수소원자 또는 C1-4직쇄 또는 분지쇄 알킬라디칼을 나타낸다.
- 제1항에 있어서, 포스겐으로 처리가 －10∼150℃ 온도에서 유기용매중에서 수행되는 방법.
- 제2항에 있어서, 용매가 염화메틸렌, 1,1,2－트리클로로에탄 또는 디옥산인 방법.
- 제1항에 있어서, 사용되는 루이스산이 염화알루미늄, 염화 제2철, 염화티탄 또는 염화제2주석인 방법.
- 제4항에 있어서, 사용되는 루이스산이 할로겐화 탄화수소, 이황화탄소, 니트로알칸 또는 테트라클로로 에틸렌인 방법.
- 제1항에 있어서, 사용되는 강산이 황산, 불화수소산, 설폰산 또는 폴리인산인 방법.
- 제1항에 있어서, 가수분해가 메탄올중에서 수산화나트륨에 의해 수행되는 방법.
- 제1항에 있어서, 하기구조식의 생성물이 중간생성물의 분리없이 제조되는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8315073A FR2552430B1 (fr) | 1983-09-22 | 1983-09-22 | Procede de preparation de quinolinones-4 |
| FR15073 | 1983-09-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850002254A true KR850002254A (ko) | 1985-05-10 |
| KR910003365B1 KR910003365B1 (ko) | 1991-05-28 |
Family
ID=9292446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840005764A KR910003365B1 (ko) | 1983-09-22 | 1984-09-20 | 4-퀴놀리논류의 제법 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4593101A (ko) |
| EP (1) | EP0140748B1 (ko) |
| JP (1) | JPS6087267A (ko) |
| KR (1) | KR910003365B1 (ko) |
| AT (1) | ATE24899T1 (ko) |
| DE (1) | DE3462035D1 (ko) |
| DK (1) | DK452684A (ko) |
| ES (1) | ES536140A0 (ko) |
| FR (1) | FR2552430B1 (ko) |
| HU (1) | HU192584B (ko) |
| IN (1) | IN162623B (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2008135762A (ru) * | 2006-02-16 | 2010-03-27 | Де МакЛин Хоспитал Корпорейшн (US) | Способы и композиции для лечения болезни паркинсона |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4013662A (en) * | 1974-12-19 | 1977-03-22 | Pfizer Inc. | Alkyl and benzyl 6,7-dialkoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylates |
| JPS51139626A (en) * | 1975-05-29 | 1976-12-02 | Sumitomo Chem Co Ltd | A herbicide and a process for its preparation |
| GB2092130B (en) * | 1980-07-28 | 1984-05-10 | Hodogaya Chemical Co Ltd | 4-oximino-1,2,3,4-tetrahydroquinoline derivatives |
| FR2498184A1 (fr) * | 1981-01-16 | 1982-07-23 | Rhone Poulenc Sante | Procede de preparation de quinolinones-4 |
-
1983
- 1983-09-22 FR FR8315073A patent/FR2552430B1/fr not_active Expired
-
1984
- 1984-09-20 AT AT84401861T patent/ATE24899T1/de active
- 1984-09-20 IN IN739/DEL/84A patent/IN162623B/en unknown
- 1984-09-20 DE DE8484401861T patent/DE3462035D1/de not_active Expired
- 1984-09-20 EP EP84401861A patent/EP0140748B1/fr not_active Expired
- 1984-09-20 KR KR1019840005764A patent/KR910003365B1/ko not_active IP Right Cessation
- 1984-09-20 JP JP59195864A patent/JPS6087267A/ja active Pending
- 1984-09-20 US US06/652,527 patent/US4593101A/en not_active Expired - Fee Related
- 1984-09-21 ES ES536140A patent/ES536140A0/es active Granted
- 1984-09-21 HU HU843578A patent/HU192584B/hu unknown
- 1984-09-21 DK DK452684A patent/DK452684A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HU192584B (en) | 1987-06-29 |
| ATE24899T1 (de) | 1987-01-15 |
| ES8505657A1 (es) | 1985-06-01 |
| IN162623B (ko) | 1988-06-18 |
| JPS6087267A (ja) | 1985-05-16 |
| HUT36094A (en) | 1985-08-28 |
| FR2552430B1 (fr) | 1985-10-25 |
| DE3462035D1 (en) | 1987-02-19 |
| DK452684D0 (da) | 1984-09-21 |
| EP0140748B1 (fr) | 1987-01-14 |
| DK452684A (da) | 1985-03-23 |
| KR910003365B1 (ko) | 1991-05-28 |
| ES536140A0 (es) | 1985-06-01 |
| US4593101A (en) | 1986-06-03 |
| FR2552430A1 (fr) | 1985-03-29 |
| EP0140748A1 (fr) | 1985-05-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR880000433A (ko) | 이미다조피리딘 및 중간체 화합물의 제조방법 | |
| KR870003989A (ko) | 치환 및 이치환 피리딘-2,3-디카르복실레이트의 제조방법과 치환된 니코티네이트의 제조방법 | |
| KR830007654A (ko) | 1,2-디히드로-3H-피롤로[1,2-a]피톤-1-카르복실 에스테르의 5-아로일화 방법 | |
| KR840000541A (ko) | N-디히드로티아졸릴-3-퀴놀린 카복사미드 유도체의 제조방법 | |
| KR850002459A (ko) | 디히드록시벤즈아미드 유도체 및 그 제조방법 | |
| KR850002254A (ko) | 4-퀴놀리논류의 제법 | |
| KR890701564A (ko) | 퀴놀린 카복실산 유도체를 제조하는 방법 | |
| KR860003239A (ko) | 퀴놀론 카복실산 유도체의 제조방법 | |
| KR860008174A (ko) | 항정신질환성 벤지소티아졸 s-산화물의 제조방법 | |
| KR890002188A (ko) | 술펜아미드 유도체 및 그의 제조방법 | |
| KR840002000A (ko) | 8-[3-(6-플루오로-1,2-벤즈이속사졸-3-일)프로필]-1-페닐-1,3,8-트리아자스피로[4,5] 데칸-4-온의 제조방법 | |
| KR850002471A (ko) | 4-퀴놀리논류의 제조방법 | |
| KR860001071A (ko) | 퀴놀론-및 나프티리돈-카르복실산의 제조방법 | |
| KR920000767A (ko) | 2-페닐-6-(피리미딘-2-일) 피리딘 유도체의 제조방법, 여기에 사용된 중간 화합물, 및 이것의 제조방법 | |
| KR890002011A (ko) | 5-할로 게노-6-아미노-니코틴산 할라이드. 이의 제조방법 및 용도 | |
| KR830002771A (ko) | 6-D-α-아미노-p-하이드록시페닐아세트아미도페니실란산의 제조방법 | |
| KR890008062A (ko) | 부분적으로 불소화된 디페닐 에테르, 이의 제조방법 및 이의 용도 | |
| ATE55372T1 (de) | Verfahren zur herstellung von 4-chlorbutanalen. | |
| KR860009006A (ko) | 2-티오크로메닐리덴아세토아세트산 에스테르의 제조방법 | |
| KR880013875A (ko) | 순수한 니트로-아미노벤젠 화합물의 제조방법 | |
| KR920019718A (ko) | 2,3,4,5- 테트라플루오로벤조산의 제조방법 | |
| KR840006214A (ko) | 4(또는 5)-(1-하이드록시알킬)이미다졸류의 제법 | |
| KR850008671A (ko) | 2-[(2-아미노에틸)-티오메틸]-5~디메틸아미노메틸 푸란의 산부가염의 제조방법 | |
| KR880001669A (ko) | 아목시실린의 제조방법 | |
| KR880001631A (ko) | 퀴놀린 유도체의 제조 방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| G160 | Decision to publish patent application | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| LAPS | Lapse due to unpaid annual fee |