JPH046707B2 - - Google Patents
Info
- Publication number
- JPH046707B2 JPH046707B2 JP62290757A JP29075787A JPH046707B2 JP H046707 B2 JPH046707 B2 JP H046707B2 JP 62290757 A JP62290757 A JP 62290757A JP 29075787 A JP29075787 A JP 29075787A JP H046707 B2 JPH046707 B2 JP H046707B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- general formula
- compound represented
- bromo
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 23
- -1 1,4-dihydro-4-oxoquinoline compound Chemical class 0.000 claims description 19
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 claims description 5
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000000911 decarboxylating effect Effects 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 239000013078 crystal Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 238000001914 filtration Methods 0.000 description 15
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000007810 chemical reaction solvent Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 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 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 4
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ROBKVGDBQLURAF-UHFFFAOYSA-N 1,4-dihydroquinoline Chemical compound C1=CC=C2CC=CNC2=C1 ROBKVGDBQLURAF-UHFFFAOYSA-N 0.000 description 2
- BUTIDJREEDINSI-UHFFFAOYSA-N 2-bromo-4,5-difluoroaniline Chemical compound NC1=CC(F)=C(F)C=C1Br BUTIDJREEDINSI-UHFFFAOYSA-N 0.000 description 2
- ZPMKGKUWDFEBFB-UHFFFAOYSA-N 2-bromo-4-chloro-5-fluoroaniline Chemical compound NC1=CC(F)=C(Cl)C=C1Br ZPMKGKUWDFEBFB-UHFFFAOYSA-N 0.000 description 2
- QNKQNJJCNWUOHC-UHFFFAOYSA-N 2-bromo-5-chloro-4-fluoroaniline Chemical compound NC1=CC(Cl)=C(F)C=C1Br QNKQNJJCNWUOHC-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- BQHDXNZNSPVVKB-UHFFFAOYSA-N diethyl 2-methylidenepropanedioate Chemical compound CCOC(=O)C(=C)C(=O)OCC BQHDXNZNSPVVKB-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XJDDLMJULQGRLU-UHFFFAOYSA-N 1,3-dioxane-4,6-dione Chemical compound O=C1CC(=O)OCO1 XJDDLMJULQGRLU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MAMRRASCBCVQHO-UHFFFAOYSA-N 2-bromo-4,5-dichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Br MAMRRASCBCVQHO-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 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 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- QEZIFBAXJMHDJP-UHFFFAOYSA-N n-chloro-4-fluoroaniline Chemical compound FC1=CC=C(NCl)C=C1 QEZIFBAXJMHDJP-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61-276684 | 1986-11-21 | ||
JP27668486 | 1986-11-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS63239269A JPS63239269A (ja) | 1988-10-05 |
JPH046707B2 true JPH046707B2 (fr) | 1992-02-06 |
Family
ID=17572877
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP62290757A Granted JPS63239269A (ja) | 1986-11-21 | 1987-11-19 | 1,4−ジヒドロ−4−オキソキノリン化合物及びその製造法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS63239269A (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69528160T2 (de) * | 1994-03-01 | 2003-02-06 | Ishihara Sangyo Kaisha | Verfahren zur herstellung von 5,7 dichlor-4-hydroxychinolin |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5758668A (en) * | 1980-07-28 | 1982-04-08 | Dynamit Nobel Ag | Manufacture of quinoline, naphthyridine and other nitrogen-bi-heterocyclic compound |
-
1987
- 1987-11-19 JP JP62290757A patent/JPS63239269A/ja active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5758668A (en) * | 1980-07-28 | 1982-04-08 | Dynamit Nobel Ag | Manufacture of quinoline, naphthyridine and other nitrogen-bi-heterocyclic compound |
Also Published As
Publication number | Publication date |
---|---|
JPS63239269A (ja) | 1988-10-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0274379B1 (fr) | Procédé de préparation de dérivés d'acide pyridine-2,3-dicarboxylique | |
JP2004507548A (ja) | オランザピン水和物の調製方法、及びこれを結晶形態のオランザピンに変換する方法 | |
JPH07196621A (ja) | 3−キノロンカルボン酸誘導体のワンポツト製造方法 | |
JPH0148911B2 (fr) | ||
JP2004500324A (ja) | ピペラジン環含有化合物の新規の合成及び結晶化 | |
US4081451A (en) | Process for preparing 2-halogeno nicotinic acids | |
JPH046707B2 (fr) | ||
JPH02215750A (ja) | 2,6−ジクロロフェニルアミノベンゼン酢酸誘導体及びジフェニルアミン誘導体の製造方法。 | |
JPH01224364A (ja) | 除草性o―カルボキシアリ―ルイミダゾリノン類の製法 | |
EP0310849B1 (fr) | Procédé pour la synthèse d'un dérivé de l'acide benzo[ij]quinolizine-2-carboxylique | |
US6861525B2 (en) | Process for the preparation imidazo[1,2-A]pyridine-3-acetamides | |
US4216340A (en) | Preparation of 5-(2,4-difluorophenyl)salicylic acid and derivatives | |
JP2842441B2 (ja) | ジアルキルオキサルアセテート類の製造方法 | |
JPH0137392B2 (fr) | ||
JPH06102656B2 (ja) | ラニチジンの製法 | |
JP2001508058A (ja) | 置換ピリミジン誘導体の製造方法 | |
JPS6110587A (ja) | 1−アザキサントン−3−カルボン酸誘導体およびその製造法 | |
JPH09510968A (ja) | (1H−テトラゾル−5−イル)テトラゾロ〔1,5−a〕キノリン類およびナフチリジン類の製造方法 | |
WO2014093565A1 (fr) | Procédés améliorés d'isolement d'acide 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-méthoxyphényl)pyridine-2-carboxylique | |
JP2815647B2 (ja) | 抗アレルギー剤中間体の製造方法 | |
JPH0330596B2 (fr) | ||
KR870001043B1 (ko) | 2-아닐리노니코틴산의 아실옥시알킬 에스테르의 제조방법 | |
JPH0212231B2 (fr) | ||
JP2001510830A (ja) | 1,3−ジアザ−スピロ(4,4)ノン−1−エン−4−オン誘導体及び1−シアノ−1−アシルアミノシクロペンタン中間体の調製方法 | |
CN114933567A (zh) | 一种2-甲硫基-4-嘧啶酮的制备方法 |