CA1167041A - Procede de preparation de la chloro-7 tetrahydro-1,2, 3,4 quinolinone-4 - Google Patents
Procede de preparation de la chloro-7 tetrahydro-1,2, 3,4 quinolinone-4Info
- Publication number
- CA1167041A CA1167041A CA000394262A CA394262A CA1167041A CA 1167041 A CA1167041 A CA 1167041A CA 000394262 A CA000394262 A CA 000394262A CA 394262 A CA394262 A CA 394262A CA 1167041 A CA1167041 A CA 1167041A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- quinolinone
- temperature
- tetrahydro
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims 2
- HOLTZTRNTRXTNX-UHFFFAOYSA-N 7-chloro-2,3-dihydro-1h-quinolin-4-one Chemical compound O=C1CCNC2=CC(Cl)=CC=C21 HOLTZTRNTRXTNX-UHFFFAOYSA-N 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 6
- -1 aromatic sulfonic acids Chemical class 0.000 claims description 5
- 230000006326 desulfonation Effects 0.000 claims description 5
- 238000005869 desulfonation reaction Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229960003677 chloroquine Drugs 0.000 description 2
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LACGRZCJQHEVKF-UHFFFAOYSA-N 4-n,4-n-diethylpentane-1,4-diamine Chemical compound CCN(CC)C(C)CCCN LACGRZCJQHEVKF-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- XVRWQISNHFVVNP-UHFFFAOYSA-N CC(C(=O)O)(NC1=CC=CC=C1)Cl Chemical compound CC(C(=O)O)(NC1=CC=CC=C1)Cl XVRWQISNHFVVNP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000009466 transformation Effects 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
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8100763 | 1981-01-16 | ||
| FR8100763A FR2498185A1 (fr) | 1981-01-16 | 1981-01-16 | Procede de preparation de la chloro-7 tetrahydro-1,2,3,4 quinolinone-4 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1167041A true CA1167041A (fr) | 1984-05-08 |
Family
ID=9254221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000394262A Expired CA1167041A (fr) | 1981-01-16 | 1982-01-15 | Procede de preparation de la chloro-7 tetrahydro-1,2, 3,4 quinolinone-4 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4421918A (en16) |
| EP (1) | EP0056764B1 (en16) |
| JP (1) | JPS57171971A (en16) |
| KR (1) | KR870001920B1 (en16) |
| AT (1) | ATE5721T1 (en16) |
| CA (1) | CA1167041A (en16) |
| DE (1) | DE3260022D1 (en16) |
| DK (1) | DK148803C (en16) |
| FR (1) | FR2498185A1 (en16) |
| HU (1) | HU184983B (en16) |
| IE (1) | IE51959B1 (en16) |
| IN (1) | IN157561B (en16) |
| ZA (1) | ZA82279B (en16) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114105871B (zh) * | 2021-12-06 | 2023-11-14 | 青岛科技大学 | 一种8-羟基喹啉的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR806715A (fr) * | 1936-01-11 | 1936-12-23 | Ig Farbenindustrie Ag | Procédé pour préparer des composés hétérocycliques de l'azote |
| US3281836A (en) * | 1948-08-26 | 1966-10-25 | Brown Robert Hanbury | Interrogation gain control |
| US2558211A (en) * | 1949-04-14 | 1951-06-26 | Lilly Co Eli | Preparation of 4-hydroxyquinoline compounds |
| FR1202105A (fr) | 1956-06-14 | 1960-01-07 | Basf Ag | Procédé pour la production de quinolones-4 comportant un groupe hydoxyle sur le noyau benzénique |
| BE638349A (en16) * | 1963-08-30 | |||
| FR1514280A (fr) * | 1967-01-10 | 1968-02-23 | Roussel Uclaf | Nouveau procédé de préparation de quinoléines substituées et produits ainsi obtenus |
-
1981
- 1981-01-16 FR FR8100763A patent/FR2498185A1/fr active Granted
-
1982
- 1982-01-14 JP JP57003537A patent/JPS57171971A/ja active Granted
- 1982-01-15 EP EP82400078A patent/EP0056764B1/fr not_active Expired
- 1982-01-15 IN IN33/DEL/82A patent/IN157561B/en unknown
- 1982-01-15 CA CA000394262A patent/CA1167041A/fr not_active Expired
- 1982-01-15 DE DE8282400078T patent/DE3260022D1/de not_active Expired
- 1982-01-15 AT AT82400078T patent/ATE5721T1/de not_active IP Right Cessation
- 1982-01-15 KR KR8200163A patent/KR870001920B1/ko not_active Expired
- 1982-01-15 DK DK16382A patent/DK148803C/da not_active IP Right Cessation
- 1982-01-15 ZA ZA82279A patent/ZA82279B/xx unknown
- 1982-01-15 IE IE77/82A patent/IE51959B1/en unknown
- 1982-01-15 HU HU82119A patent/HU184983B/hu not_active IP Right Cessation
- 1982-01-15 US US06/339,704 patent/US4421918A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HU184983B (en) | 1984-11-28 |
| KR830009034A (ko) | 1983-12-17 |
| US4421918A (en) | 1983-12-20 |
| EP0056764A1 (fr) | 1982-07-28 |
| IN157561B (en16) | 1986-04-26 |
| DK148803B (da) | 1985-10-07 |
| DK148803C (da) | 1986-04-01 |
| JPH0155270B2 (en16) | 1989-11-22 |
| KR870001920B1 (ko) | 1987-10-22 |
| IE820077L (en) | 1982-07-16 |
| FR2498185A1 (fr) | 1982-07-23 |
| EP0056764B1 (fr) | 1983-12-28 |
| ATE5721T1 (de) | 1984-01-15 |
| IE51959B1 (en) | 1987-04-29 |
| JPS57171971A (en) | 1982-10-22 |
| DK16382A (da) | 1982-07-17 |
| ZA82279B (en) | 1982-11-24 |
| DE3260022D1 (en) | 1984-02-02 |
| FR2498185B1 (en16) | 1983-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |