CH615917A5 - Process for preparing novel quinoline derivatives - Google Patents
Process for preparing novel quinoline derivatives Download PDFInfo
- Publication number
- CH615917A5 CH615917A5 CH1168574A CH1168574A CH615917A5 CH 615917 A5 CH615917 A5 CH 615917A5 CH 1168574 A CH1168574 A CH 1168574A CH 1168574 A CH1168574 A CH 1168574A CH 615917 A5 CH615917 A5 CH 615917A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- formula
- ring closure
- subjected
- ethoxy
- Prior art date
Links
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 4
- 230000002378 acidificating effect Effects 0.000 claims 3
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 239000012188 paraffin wax Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 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 1
- 239000000047 product Substances 0.000 description 14
- 239000000155 melt Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- -1 hydroxyl compound Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- VCYQNCHWCSKOTO-UHFFFAOYSA-N 4-amino-2-ethoxyphenol Chemical compound CCOC1=CC(N)=CC=C1O VCYQNCHWCSKOTO-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- GAKQMSVBEZWYGU-UHFFFAOYSA-N C(C)(=O)OC1=C(C=C(N)C=C1)OCC Chemical compound C(C)(=O)OC1=C(C=C(N)C=C1)OCC GAKQMSVBEZWYGU-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- CAWVNWVFAVJLIL-UHFFFAOYSA-N dibenzyl 2-(ethoxymethylidene)propanedioate Chemical compound C=1C=CC=CC=1COC(=O)C(=COCC)C(=O)OCC1=CC=CC=C1 CAWVNWVFAVJLIL-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 230000002192 coccidiostatic effect Effects 0.000 description 2
- JHAYEQICABJSTP-UHFFFAOYSA-N decoquinate Chemical compound N1C=C(C(=O)OCC)C(=O)C2=C1C=C(OCC)C(OCCCCCCCCCC)=C2 JHAYEQICABJSTP-UHFFFAOYSA-N 0.000 description 2
- 229960001878 decoquinate Drugs 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- OGFGOEBARPUXOW-UHFFFAOYSA-N ethyl 6-acetyloxy-7-ethoxy-4-oxo-1H-quinoline-3-carboxylate Chemical compound C(C)(=O)OC=1C=C2C(=C(C=NC2=CC1OCC)C(=O)OCC)O OGFGOEBARPUXOW-UHFFFAOYSA-N 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
- GIHYKBDWFSOKNN-UHFFFAOYSA-N 2-ethoxy-4-nitrophenol Chemical compound CCOC1=CC([N+]([O-])=O)=CC=C1O GIHYKBDWFSOKNN-UHFFFAOYSA-N 0.000 description 1
- MHYNVHMGKMPURK-UHFFFAOYSA-N 3-ethoxy-2-ethoxycarbonylprop-2-enoic acid Chemical compound CCOC=C(C(O)=O)C(=O)OCC MHYNVHMGKMPURK-UHFFFAOYSA-N 0.000 description 1
- 150000004333 6-hydroxyquinolines Chemical class 0.000 description 1
- FKHZSVWGOFCGCJ-UHFFFAOYSA-N C(C)(=O)OC1=C(C=C(C=C1)[N+](=O)[O-])OCC Chemical compound C(C)(=O)OC1=C(C=C(C=C1)[N+](=O)[O-])OCC FKHZSVWGOFCGCJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 229960003683 amprolium Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- AZCOMUGSJJOYHH-UHFFFAOYSA-N diethyl 2-[(3-ethoxy-4-hydroxyanilino)methylidene]propanedioate Chemical compound CCOC(=O)C(=CNC1=CC(OCC)=C(O)C=C1)C(=O)OCC AZCOMUGSJJOYHH-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HLASKCWWYKMAFY-UHFFFAOYSA-N ethyl 7-ethoxy-6-hydroxy-4-oxo-3h-quinoline-3-carboxylate Chemical compound CCOC1=C(O)C=C2C(=O)C(C(=O)OCC)C=NC2=C1 HLASKCWWYKMAFY-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- PJBQYZZKGNOKNJ-UHFFFAOYSA-M hydron;5-[(2-methylpyridin-1-ium-1-yl)methyl]-2-propylpyrimidin-4-amine;dichloride Chemical compound Cl.[Cl-].NC1=NC(CCC)=NC=C1C[N+]1=CC=CC=C1C PJBQYZZKGNOKNJ-UHFFFAOYSA-M 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001404 HU167573B (enrdf_load_stackoverflow) | 1973-08-28 | 1973-08-28 | |
| HUCI001403 HU167572B (enrdf_load_stackoverflow) | 1973-08-28 | 1973-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615917A5 true CH615917A5 (en) | 1980-02-29 |
Family
ID=26318396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1168574A CH615917A5 (en) | 1973-08-28 | 1974-08-27 | Process for preparing novel quinoline derivatives |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55120566A (en) | 1979-03-09 | 1980-09-17 | Mitsui Toatsu Chem Inc | New quinoline derivative |
| DE4014171A1 (de) * | 1990-05-03 | 1991-11-07 | Basf Ag | Cyanochinolinverbindungen |
-
1974
- 1974-08-23 SE SE7410745A patent/SE406911B/xx unknown
- 1974-08-26 NL NL7411324A patent/NL7411324A/xx not_active Application Discontinuation
- 1974-08-26 PL PL1974187261A patent/PL92578B1/pl unknown
- 1974-08-26 AT AT688374A patent/AT338789B/de not_active IP Right Cessation
- 1974-08-27 GB GB3745174A patent/GB1467225A/en not_active Expired
- 1974-08-27 DK DK454774AA patent/DK141167B/da not_active IP Right Cessation
- 1974-08-27 CH CH1168574A patent/CH615917A5/de not_active IP Right Cessation
- 1974-08-27 NO NO743064A patent/NO145788C/no unknown
- 1974-08-27 CA CA207,894A patent/CA1044239A/en not_active Expired
- 1974-08-27 SU SU7402057994A patent/SU567402A3/ru active
- 1974-08-27 JP JP49098309A patent/JPS5082077A/ja active Pending
- 1974-08-28 DD DD180757A patent/DD114077A1/xx unknown
- 1974-08-28 IN IN1940/CAL/1974A patent/IN140826B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1044239A (en) | 1978-12-12 |
| NO145788B (no) | 1982-02-22 |
| JPS5082077A (enrdf_load_stackoverflow) | 1975-07-03 |
| GB1467225A (en) | 1977-03-16 |
| DK141167B (da) | 1980-01-28 |
| DD114077A1 (enrdf_load_stackoverflow) | 1975-07-12 |
| SE7410745L (enrdf_load_stackoverflow) | 1975-03-03 |
| NL7411324A (nl) | 1975-03-04 |
| PL92578B1 (enrdf_load_stackoverflow) | 1977-04-30 |
| IN140826B (enrdf_load_stackoverflow) | 1976-12-25 |
| SE406911B (sv) | 1979-03-05 |
| SU567402A3 (ru) | 1977-07-30 |
| AT338789B (de) | 1977-09-12 |
| DK454774A (enrdf_load_stackoverflow) | 1975-04-28 |
| DK141167C (enrdf_load_stackoverflow) | 1980-06-23 |
| NO145788C (no) | 1982-06-02 |
| ATA688374A (de) | 1977-01-15 |
| NO743064L (enrdf_load_stackoverflow) | 1975-03-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |