DK141167B - Mellemprodukt til anvendelse ved fremstilling af 6,7-dialkoxy-4-hydroxykinolinsyreestre. - Google Patents
Mellemprodukt til anvendelse ved fremstilling af 6,7-dialkoxy-4-hydroxykinolinsyreestre. Download PDFInfo
- Publication number
- DK141167B DK141167B DK454774AA DK454774A DK141167B DK 141167 B DK141167 B DK 141167B DK 454774A A DK454774A A DK 454774AA DK 454774 A DK454774 A DK 454774A DK 141167 B DK141167 B DK 141167B
- Authority
- DK
- Denmark
- Prior art keywords
- dialkoxy
- ethoxy
- carboxylic acid
- ester
- general formula
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- -1 ethoxymethylene Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 238000005804 alkylation reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000004576 sand Substances 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- VCYQNCHWCSKOTO-UHFFFAOYSA-N 4-amino-2-ethoxyphenol Chemical compound CCOC1=CC(N)=CC=C1O VCYQNCHWCSKOTO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 2
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- 239000002253 acid Substances 0.000 description 2
- 150000001347 alkyl bromides Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005382 thermal cycling Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 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 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-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
- YSMYCXWVNAACEP-UHFFFAOYSA-N 4-decoxy-3-ethoxyaniline Chemical compound CCCCCCCCCCOC1=CC=C(N)C=C1OCC YSMYCXWVNAACEP-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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- KVNJFSCNSVLFCT-UHFFFAOYSA-N benzyl 6-decoxy-7-ethoxyquinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC(=O)C=1C=NC2=CC(=C(C=C2C1)OCCCCCCCCCC)OCC KVNJFSCNSVLFCT-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003224 coccidiostatic agent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 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 1
- 239000007857 degradation product Substances 0.000 description 1
- 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 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- GLUQMYQDGHKVIX-UHFFFAOYSA-N ethyl 7-ethoxy-6-hydroxy-4-oxo-1h-quinoline-3-carboxylate Chemical compound CCOC1=C(O)C=C2C(=O)C(C(=O)OCC)=CNC2=C1 GLUQMYQDGHKVIX-UHFFFAOYSA-N 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
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 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 description 1
- 239000008096 xylene 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)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001404 HU167573B (enrdf_load_html_response) | 1973-08-28 | 1973-08-28 | |
| HUCI001403 | 1973-08-28 | ||
| HUCI001404 | 1973-08-28 | ||
| HUCI001403 HU167572B (enrdf_load_html_response) | 1973-08-28 | 1973-08-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK454774A DK454774A (enrdf_load_html_response) | 1975-04-28 |
| DK141167B true DK141167B (da) | 1980-01-28 |
| DK141167C DK141167C (enrdf_load_html_response) | 1980-06-23 |
Family
ID=26318396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK454774AA DK141167B (da) | 1973-08-28 | 1974-08-27 | Mellemprodukt til anvendelse ved fremstilling af 6,7-dialkoxy-4-hydroxykinolinsyreestre. |
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 AT AT688374A patent/AT338789B/de not_active IP Right Cessation
- 1974-08-26 NL NL7411324A patent/NL7411324A/xx not_active Application Discontinuation
- 1974-08-26 PL PL1974187261A patent/PL92578B1/pl unknown
- 1974-08-27 SU SU7402057994A patent/SU567402A3/ru active
- 1974-08-27 CA CA207,894A patent/CA1044239A/en not_active Expired
- 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 DK DK454774AA patent/DK141167B/da not_active IP Right Cessation
- 1974-08-27 GB GB3745174A patent/GB1467225A/en not_active Expired
- 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 |
|---|---|
| JPS5082077A (enrdf_load_html_response) | 1975-07-03 |
| SU567402A3 (ru) | 1977-07-30 |
| NO743064L (enrdf_load_html_response) | 1975-03-24 |
| SE7410745L (enrdf_load_html_response) | 1975-03-03 |
| NO145788B (no) | 1982-02-22 |
| DK454774A (enrdf_load_html_response) | 1975-04-28 |
| SE406911B (sv) | 1979-03-05 |
| CA1044239A (en) | 1978-12-12 |
| DK141167C (enrdf_load_html_response) | 1980-06-23 |
| GB1467225A (en) | 1977-03-16 |
| ATA688374A (de) | 1977-01-15 |
| AT338789B (de) | 1977-09-12 |
| IN140826B (enrdf_load_html_response) | 1976-12-25 |
| CH615917A5 (en) | 1980-02-29 |
| DD114077A1 (enrdf_load_html_response) | 1975-07-12 |
| NO145788C (no) | 1982-06-02 |
| NL7411324A (nl) | 1975-03-04 |
| PL92578B1 (enrdf_load_html_response) | 1977-04-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69723846T2 (de) | Verfahren zur Herstellung von Sildenafil | |
| US3075992A (en) | Esters of indoles | |
| NO156328B (no) | Konstruksjon med keramisk overflatebelegg samt fremgangsmaate til fremstilling av samme. | |
| Gowenlock et al. | 167. Syntheses of 2-monosubstituted and 2: 3-disubstituted quinoxalines | |
| Taylor et al. | The Synthesis of 4-Aminoisoxazolo [5, 4-d] pyrimidines1 | |
| KR20160017061A (ko) | ''3-(5-치환 옥시-2,4-디니트로-페닐)-2-옥소-프로피온산 에스테르'' 화합물, 그 방법 및 활용 | |
| DE1770595A1 (de) | Substituierte Tetrahydrochinoline | |
| US2852520A (en) | Trialkoxybenzoyloxyalkyl derivatives related to norharman | |
| DK141167B (da) | Mellemprodukt til anvendelse ved fremstilling af 6,7-dialkoxy-4-hydroxykinolinsyreestre. | |
| SU493974A3 (ru) | Способ получени производных тиазоло (5,4-д) пиримидина | |
| JPS634544B2 (enrdf_load_html_response) | ||
| NO130727B (enrdf_load_html_response) | ||
| SU474142A3 (ru) | Способ получени производных 2-/5-нитро-2-фурил/-тиено/2,3-пиримидина | |
| US2740781A (en) | 3, 26-dihydroxy-16, 22-imino-5-cholestenes, 3, 26-dihydroxy-16, 22-imino-5, 16, 20(22)-cholestatrienes and derivatives thereof | |
| NO119797B (enrdf_load_html_response) | ||
| JPS5822107B2 (ja) | α↓−アミノメチレン↓−β↓−ホルミルアミノプロピオニトリル及びその製法 | |
| NO771771L (no) | Fremgangsm}te for fremstilling av nye derivater av dibenzo(de, h)kinolin | |
| US2696488A (en) | 2, 4, 6-tris-(1-piperidyl)-5-benzylpyrimidine and process of preparing same | |
| DK156391B (da) | Analogifremgangsmaade til fremstilling af 3-aminopyrrolderivater | |
| EP0026675B1 (en) | 1-azaxanthone-3-carboxylic acids, their preparation and pharmaceutical compositions containing them | |
| Baker et al. | 6-Methoxy-8-nitroquinolines with Substituents in the 3-and 4-Positions | |
| DE3023567A1 (de) | Substituierte (beta) -carbolin-3-carbonsaeurederivate | |
| Hart et al. | SOME DERIVATIVES OF SALIGENIN. | |
| Cheney et al. | Some Tetrahydrothiophene β-Keto Ester Derivatives | |
| SU421186A3 (ru) | Способ получения производных 17-аза-16-кетостероидов |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |