SU567402A3 - Способ получени производных хинолина или их солей - Google Patents
Способ получени производных хинолина или их солейInfo
- Publication number
- SU567402A3 SU567402A3 SU7402057994A SU2057994A SU567402A3 SU 567402 A3 SU567402 A3 SU 567402A3 SU 7402057994 A SU7402057994 A SU 7402057994A SU 2057994 A SU2057994 A SU 2057994A SU 567402 A3 SU567402 A3 SU 567402A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- general formula
- reaction
- mol
- ethoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 7
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 150000003839 salts Chemical class 0.000 title description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 16
- -1 esters of 6 Chemical class 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 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 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-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
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 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 2
- 239000003085 diluting agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YIFCWYUSYGFFMH-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedioic acid Chemical compound CCOC=C(C(O)=O)C(O)=O YIFCWYUSYGFFMH-UHFFFAOYSA-N 0.000 description 1
- GIHYKBDWFSOKNN-UHFFFAOYSA-N 2-ethoxy-4-nitrophenol Chemical compound CCOC1=CC([N+]([O-])=O)=CC=C1O GIHYKBDWFSOKNN-UHFFFAOYSA-N 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
- 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 1
- MEEXQFKGGJULFM-UHFFFAOYSA-N CCOC1=C(C=CC(=C1)NC=C(C(=O)O)C(=O)O)OC(=O)C Chemical compound CCOC1=C(C=CC(=C1)NC=C(C(=O)O)C(=O)O)OC(=O)C MEEXQFKGGJULFM-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- WZZXNOPGKYPHRW-UHFFFAOYSA-N benzyl 7-ethoxy-6-hydroxy-4-oxo-3H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC(=O)C1C=NC2=CC(=C(C=C2C1=O)O)OCC WZZXNOPGKYPHRW-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- OGFGOEBARPUXOW-UHFFFAOYSA-N ethyl 6-acetyloxy-7-ethoxy-4-oxo-1H-quinoline-3-carboxylate Chemical group C(C)(=O)OC=1C=C2C(=C(C=NC2=CC1OCC)C(=O)OCC)O OGFGOEBARPUXOW-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 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 |
|---|---|
| SU567402A3 true SU567402A3 (ru) | 1977-07-30 |
Family
ID=26318396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7402057994A SU567402A3 (ru) | 1973-08-28 | 1974-08-27 | Способ получени производных хинолина или их солей |
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 |
| CH615917A5 (en) | 1980-02-29 |
| 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 |
| 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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