ZA200300328B - Process for the preparation of quinoline derivatives. - Google Patents
Process for the preparation of quinoline derivatives. Download PDFInfo
- Publication number
- ZA200300328B ZA200300328B ZA200300328A ZA200300328A ZA200300328B ZA 200300328 B ZA200300328 B ZA 200300328B ZA 200300328 A ZA200300328 A ZA 200300328A ZA 200300328 A ZA200300328 A ZA 200300328A ZA 200300328 B ZA200300328 B ZA 200300328B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compound
- amount
- water
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 12
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 6
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 241000209140 Triticum Species 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 150000003248 quinolines Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CTQMJYWDVABFRZ-UHFFFAOYSA-N cloxiquine Chemical compound C1=CN=C2C(O)=CC=C(Cl)C2=C1 CTQMJYWDVABFRZ-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 150000004325 8-hydroxyquinolines Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- -1 hydroxyl ions Chemical class 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GKOMRSJNZZXVMU-UHFFFAOYSA-N heptan-2-yl 2-chloroacetate Chemical compound CCCCCC(C)OC(=O)CCl GKOMRSJNZZXVMU-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7
-
- 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
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH12742000 | 2000-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200300328B true ZA200300328B (en) | 2004-03-31 |
Family
ID=4565202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200300328A ZA200300328B (en) | 2000-06-28 | 2003-01-13 | Process for the preparation of quinoline derivatives. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6660865B2 (pt) |
| EP (1) | EP1294694B1 (pt) |
| JP (1) | JP3955814B2 (pt) |
| KR (1) | KR100572818B1 (pt) |
| CN (1) | CN1256327C (pt) |
| AR (1) | AR029283A1 (pt) |
| AT (1) | ATE280760T1 (pt) |
| AU (1) | AU780534B2 (pt) |
| BR (2) | BR0112064B1 (pt) |
| CA (1) | CA2412543C (pt) |
| DE (1) | DE60106760T2 (pt) |
| DK (1) | DK1294694T3 (pt) |
| ES (1) | ES2228923T3 (pt) |
| HU (1) | HU230214B1 (pt) |
| IL (2) | IL153424A0 (pt) |
| MX (1) | MXPA02012398A (pt) |
| PL (1) | PL200447B1 (pt) |
| PT (1) | PT1294694E (pt) |
| RU (1) | RU2263110C2 (pt) |
| TW (1) | TWI230154B (pt) |
| UA (1) | UA73587C2 (pt) |
| WO (1) | WO2002000625A2 (pt) |
| ZA (1) | ZA200300328B (pt) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8729097B2 (en) | 2008-10-06 | 2014-05-20 | The Johns Hopkins University | Quinoline compounds as inhibitors of angiogenesis, human methionine aminopeptidase, and SIRT1, and methods of treating disorders |
| CN101805288A (zh) * | 2010-04-21 | 2010-08-18 | 新沂市永诚化工有限公司 | 一种合成解毒喹的新方法 |
| GB201119690D0 (en) | 2011-11-14 | 2011-12-28 | Syngenta Participations Ag | Process for the preparation of compounds |
| CN102718706B (zh) * | 2012-05-31 | 2014-05-07 | 绍兴文理学院 | 一种2-(5-氯-8-喹啉氧基)乙酸的制备方法 |
| CN103524411B (zh) * | 2013-10-21 | 2015-03-04 | 哈尔滨理工大学 | 一种5-氯-8-喹啉氧基乙酸的合成方法 |
| CN105001158B (zh) * | 2015-07-09 | 2018-02-02 | 北京颖泰嘉和生物科技股份有限公司 | 一种合成解草酯的方法 |
| CN113135851A (zh) * | 2021-04-26 | 2021-07-20 | 甘肃联凯生物科技有限公司 | 一种解毒喹的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3382743D1 (de) | 1982-05-07 | 1994-05-11 | Ciba Geigy | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen. |
| EP0492366B1 (de) * | 1990-12-21 | 1997-03-26 | Hoechst Schering AgrEvo GmbH | Neue 5-Chlorchinolin-8-oxyalkancarbonsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Antidots von Herbiziden |
-
2001
- 2001-06-26 DE DE60106760T patent/DE60106760T2/de not_active Expired - Lifetime
- 2001-06-26 BR BRPI0112064-6A patent/BR0112064B1/pt not_active IP Right Cessation
- 2001-06-26 JP JP2002505373A patent/JP3955814B2/ja not_active Expired - Lifetime
- 2001-06-26 KR KR1020027017703A patent/KR100572818B1/ko not_active IP Right Cessation
- 2001-06-26 AT AT01957889T patent/ATE280760T1/de active
- 2001-06-26 AU AU79689/01A patent/AU780534B2/en not_active Expired
- 2001-06-26 HU HU0300703A patent/HU230214B1/hu unknown
- 2001-06-26 PL PL363224A patent/PL200447B1/pl unknown
- 2001-06-26 MX MXPA02012398A patent/MXPA02012398A/es active IP Right Grant
- 2001-06-26 UA UA2003010722A patent/UA73587C2/uk unknown
- 2001-06-26 BR BRPI0112064A patent/BRPI0112064B8/pt unknown
- 2001-06-26 AR ARP010103033A patent/AR029283A1/es active IP Right Grant
- 2001-06-26 IL IL15342401A patent/IL153424A0/xx active IP Right Grant
- 2001-06-26 CA CA2412543A patent/CA2412543C/en not_active Expired - Lifetime
- 2001-06-26 TW TW090115381A patent/TWI230154B/zh not_active IP Right Cessation
- 2001-06-26 RU RU2003100505/04A patent/RU2263110C2/ru active
- 2001-06-26 EP EP01957889A patent/EP1294694B1/en not_active Expired - Lifetime
- 2001-06-26 ES ES01957889T patent/ES2228923T3/es not_active Expired - Lifetime
- 2001-06-26 WO PCT/EP2001/007258 patent/WO2002000625A2/en active IP Right Grant
- 2001-06-26 CN CNB018119549A patent/CN1256327C/zh not_active Expired - Lifetime
- 2001-06-26 DK DK01957889T patent/DK1294694T3/da active
- 2001-06-26 US US10/312,122 patent/US6660865B2/en not_active Expired - Lifetime
- 2001-06-26 PT PT01957889T patent/PT1294694E/pt unknown
-
2002
- 2002-12-12 IL IL153424A patent/IL153424A/en unknown
-
2003
- 2003-01-13 ZA ZA200300328A patent/ZA200300328B/en unknown
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