JPS6152827B2 - - Google Patents
Info
- Publication number
- JPS6152827B2 JPS6152827B2 JP8744079A JP8744079A JPS6152827B2 JP S6152827 B2 JPS6152827 B2 JP S6152827B2 JP 8744079 A JP8744079 A JP 8744079A JP 8744079 A JP8744079 A JP 8744079A JP S6152827 B2 JPS6152827 B2 JP S6152827B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- compound represented
- methyl
- following
- 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
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000007514 bases Chemical class 0.000 claims description 8
- 239000003125 aqueous solvent Substances 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- -1 methoxyethoxy, butoxy groups Chemical group 0.000 description 6
- 239000004471 Glycine Substances 0.000 description 5
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
- ZNEOZWHWBWZONP-UHFFFAOYSA-N CC=1C=C(O)N(CC(O)=O)C(=O)C=1C#N Chemical compound CC=1C=C(O)N(CC(O)=O)C(=O)C=1C#N ZNEOZWHWBWZONP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-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
- 230000002378 acidificating effect Effects 0.000 description 2
- 229940000635 beta-alanine Drugs 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N glutamic acid Chemical compound OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical compound OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 1
- UMCLCZMPTREESK-UHFFFAOYSA-N 2-ethoxyethyl 2-cyanoacetate Chemical compound CCOCCOC(=O)CC#N UMCLCZMPTREESK-UHFFFAOYSA-N 0.000 description 1
- KBUWQCXQODASRJ-UHFFFAOYSA-N 6-hydroxy-5-methyl-1h-pyridin-2-one Chemical compound CC1=CC=C(O)N=C1O KBUWQCXQODASRJ-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- REIYHFWZISXFKU-UHFFFAOYSA-N Butyl acetoacetate Chemical compound CCCCOC(=O)CC(C)=O REIYHFWZISXFKU-UHFFFAOYSA-N 0.000 description 1
- OYJWWEUFIDFWTQ-UHFFFAOYSA-N CC=1C=C(O)N(CC(O)=O)C(=O)C=1C(N)=O Chemical compound CC=1C=C(O)N(CC(O)=O)C(=O)C=1C(N)=O OYJWWEUFIDFWTQ-UHFFFAOYSA-N 0.000 description 1
- WONCXRLGPXEDCT-UHFFFAOYSA-N CC=1C=C(O)N(CCC(O)=O)C(=O)C=1C#N Chemical compound CC=1C=C(O)N(CCC(O)=O)C(=O)C=1C#N WONCXRLGPXEDCT-UHFFFAOYSA-N 0.000 description 1
- LNCGNOYEYPNQEA-UHFFFAOYSA-N CN1C(O)=CC=C(C#N)C1=O Chemical compound CN1C(O)=CC=C(C#N)C1=O LNCGNOYEYPNQEA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PJOUURZOYJMYPA-UHFFFAOYSA-N OClC#N Chemical group OClC#N PJOUURZOYJMYPA-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NLFIMXLLXGTDME-UHFFFAOYSA-N propyl 2-cyanoacetate Chemical compound CCCOC(=O)CC#N NLFIMXLLXGTDME-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
- 239000002994 raw material Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8744079A JPS5612369A (en) | 1979-07-12 | 1979-07-12 | Preparation of 6-hydroxy-pyrido-2-one compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8744079A JPS5612369A (en) | 1979-07-12 | 1979-07-12 | Preparation of 6-hydroxy-pyrido-2-one compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5612369A JPS5612369A (en) | 1981-02-06 |
| JPS6152827B2 true JPS6152827B2 (fr) | 1986-11-14 |
Family
ID=13914909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8744079A Granted JPS5612369A (en) | 1979-07-12 | 1979-07-12 | Preparation of 6-hydroxy-pyrido-2-one compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5612369A (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0313051A1 (fr) | 1987-10-20 | 1989-04-26 | Fuji Photo Film Co., Ltd. | Matériau photographique à l'halogénure d'argent |
| EP0435334A2 (fr) | 1989-12-29 | 1991-07-03 | Fuji Photo Film Co., Ltd. | Produit photographique couleur à l'halogénure d'argent contenant un coupleur cyan coloré en jaune |
-
1979
- 1979-07-12 JP JP8744079A patent/JPS5612369A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0313051A1 (fr) | 1987-10-20 | 1989-04-26 | Fuji Photo Film Co., Ltd. | Matériau photographique à l'halogénure d'argent |
| EP0435334A2 (fr) | 1989-12-29 | 1991-07-03 | Fuji Photo Film Co., Ltd. | Produit photographique couleur à l'halogénure d'argent contenant un coupleur cyan coloré en jaune |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5612369A (en) | 1981-02-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9643937B1 (en) | One-pot process for preparation of ammonium and hydroxyl ammonium derivatives of bis 5,5′-tetrazole-1,1′-dihydroxide | |
| US4264771A (en) | Alkylation of substituted oxazolinone-(5) compounds | |
| JPH05208978A (ja) | １，２−ジヒドロ−３Ｈ−ピロロ〔１，２−α〕ピロール−１−カルボン酸エステルの５位のアロイル化方法 | |
| JPS6152827B2 (fr) | ||
| JPS648616B2 (fr) | ||
| BR112020010618B1 (pt) | Método para preparar acetato de salicilamina | |
| JPH01156965A (ja) | チオヒダントイン化合物 | |
| RU2032679C1 (ru) | Производные бензатиазинов | |
| SU650504A3 (ru) | Способ получени метил-(2-хиноксалинилметилен)-карбазат-диоксида | |
| JPS6051475B2 (ja) | 新規なフエニル酢酸誘導体 | |
| SE435278B (sv) | 5-cyano-1-legre(c?711?71-?714)alkyl-pyrrol-2-ettiksyra, framstellning derav och anvendningen som mellanprodukt vid framstellning av terapeutiskt verksamma pyrrolderivat | |
| CZ2004218A3 (en) | Process for preparing 4-chloro-N-(4,5-dihydro-1-H-imidazol-2-yl)-6-methoxy-2-methyl-5-pyrimidinamine | |
| JPH01316352A (ja) | ３‐シアノ‐４‐アリールピロールの製造法 | |
| Koelsch | The Stability of 1-Nitrosopiperidine to Ethyl Sodiomalonate | |
| JP2565372B2 (ja) | チオール化合物の製造方法 | |
| JPS6034958A (ja) | ３，４―ジヒドロ―２―置換―２ｈ―１，２―ベンゾチアジン―カルボン酸 １，１―ジオキサイド誘導体の製造法 | |
| JP3023773B2 (ja) | 含窒素複素環化合物 | |
| JPS58154537A (ja) | オキシ安息香酸低級アルアルキルエステルの製造法 | |
| JPS6155A (ja) | 芳香族アミンの製造方法 | |
| JP3328694B2 (ja) | 含窒素複素環化合物の製造方法 | |
| KR810000291B1 (ko) | 3, 4-디하이드로-2-메틸-4-옥소-2h-1, 2-벤조티아진-3-카복실산-1, 1-디옥사이드의 제조방법 | |
| JPS62207237A (ja) | β−アルコキシアクロレイン誘導体の製造法 | |
| JPS6344579A (ja) | １−アザビシクロノナン類およびその製造法 | |
| JPS60115567A (ja) | ３−アミノイソオキサゾ−ル類の製法 | |
| JPS6312869B2 (fr) |