JPH0548224B2 - - Google Patents
Info
- Publication number
- JPH0548224B2 JPH0548224B2 JP14916585A JP14916585A JPH0548224B2 JP H0548224 B2 JPH0548224 B2 JP H0548224B2 JP 14916585 A JP14916585 A JP 14916585A JP 14916585 A JP14916585 A JP 14916585A JP H0548224 B2 JPH0548224 B2 JP H0548224B2
- Authority
- JP
- Japan
- Prior art keywords
- pyridyl
- added
- reaction
- distilled
- reduced pressure
- 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
- -1 4-pyridylpimelic acid ester Chemical class 0.000 claims description 15
- RGEJCUIWCMDOOK-UHFFFAOYSA-N 2-pyridin-4-ylcyclohexan-1-one Chemical compound O=C1CCCCC1C1=CC=NC=C1 RGEJCUIWCMDOOK-UHFFFAOYSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- SEIUJHIHBPGGDJ-UHFFFAOYSA-N 2-pyridin-4-ylphenol Chemical class OC1=CC=CC=C1C1=CC=NC=C1 SEIUJHIHBPGGDJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012450 pharmaceutical intermediate Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LXSZVOUDYGKZNI-UHFFFAOYSA-N 1-methyl-3-oxo-7-pyridin-4-yl-5,6,7,8-tetrahydro-2h-isoquinoline-4-carbonitrile Chemical compound C1C2=C(C)NC(=O)C(C#N)=C2CCC1C1=CC=NC=C1 LXSZVOUDYGKZNI-UHFFFAOYSA-N 0.000 description 2
- UKVQBONVSSLJBB-UHFFFAOYSA-N 2-pyridin-2-ylacetonitrile Chemical compound N#CCC1=CC=CC=N1 UKVQBONVSSLJBB-UHFFFAOYSA-N 0.000 description 2
- BHIIMPOVZNJDSZ-UHFFFAOYSA-N 4-pyridin-2-ylcyclohexan-1-one Chemical compound C1CC(=O)CCC1C1=CC=CC=N1 BHIIMPOVZNJDSZ-UHFFFAOYSA-N 0.000 description 2
- RSDGRRJTGIGGBP-UHFFFAOYSA-N 4-pyridin-4-ylcyclohexan-1-one Chemical compound C1CC(=O)CCC1C1=CC=NC=C1 RSDGRRJTGIGGBP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000003177 cardiotonic effect Effects 0.000 description 2
- GBCKMCXGDXVDPG-UHFFFAOYSA-N dimethyl 4-pyridin-4-ylheptanedioate Chemical compound COC(=O)CCC(CCC(=O)OC)C1=CC=NC=C1 GBCKMCXGDXVDPG-UHFFFAOYSA-N 0.000 description 2
- SHWINQXIGSEZAP-UHFFFAOYSA-N dimethyl heptanedioate Chemical compound COC(=O)CCCCCC(=O)OC SHWINQXIGSEZAP-UHFFFAOYSA-N 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- DRLVMOAWNVOSPE-UHFFFAOYSA-N 2-phenylcyclohexan-1-one Chemical class O=C1CCCCC1C1=CC=CC=C1 DRLVMOAWNVOSPE-UHFFFAOYSA-N 0.000 description 1
- BMVSAKPRNWZCPG-UHFFFAOYSA-N 2-pyridin-4-ylacetonitrile Chemical compound N#CCC1=CC=NC=C1 BMVSAKPRNWZCPG-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-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
- 239000002253 acid Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical class OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical group O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 description 1
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- LKKOGZVQGQUVHF-UHFFFAOYSA-N diethyl heptanedioate Chemical compound CCOC(=O)CCCCCC(=O)OCC LKKOGZVQGQUVHF-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14916585A JPS6210063A (ja) | 1985-07-09 | 1985-07-09 | ４−ピリジルシクロヘキサノンを製造する方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14916585A JPS6210063A (ja) | 1985-07-09 | 1985-07-09 | ４−ピリジルシクロヘキサノンを製造する方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6210063A JPS6210063A (ja) | 1987-01-19 |
| JPH0548224B2 true JPH0548224B2 (he) | 1993-07-20 |
Family
ID=15469216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14916585A Granted JPS6210063A (ja) | 1985-07-09 | 1985-07-09 | ４−ピリジルシクロヘキサノンを製造する方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6210063A (he) |
-
1985
- 1985-07-09 JP JP14916585A patent/JPS6210063A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6210063A (ja) | 1987-01-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU180905B (en) | Process for preparing vincadifformine | |
| WO2010055042A1 (en) | 2-[(1-cyanopropyl)carbamoyl]-5-methoxymethyl nicotinic acids and the use thereof in manufacturing herbicidal imidazolinones | |
| Toya et al. | Stereocontrolled total synthesis and biological evaluation of (−)-and (+)-petrosin and its derivatives | |
| JP2825517B2 (ja) | 除草性ｏ―カルボキシアリ―ルイミダゾリノン類の製法 | |
| Raboin et al. | On the way to unsymmetrical terpyridines carrying carboxylic acids | |
| JPS61129145A (ja) | ヒドロキノン誘導体及びその製造方法 | |
| JPH0548224B2 (he) | ||
| JP3219946B2 (ja) | 新規製造中間体及びピリジン誘導体の製造方法 | |
| EP1732899B1 (en) | Process for preparing cyclohexanediacetic acid monoamide | |
| Chapman et al. | Reactions of β-keto esters with 2-cyano-1, 2, 5, 6-tetrahydropyridines | |
| US4283536A (en) | Preparation of vincadifformine and related derivatives | |
| US5625069A (en) | Process for preparing 2-cyano-3,5-dimethyl-4-methoxypyridine | |
| JP2523026B2 (ja) | α，β―不飽和ケトン及びケトオキシム誘導体 | |
| NO750877L (he) | ||
| JPH082882B2 (ja) | ピリジン−２，３−ジカルボン酸誘導体の製法 | |
| EP0281661B1 (en) | 2-alkoxycarbonyl-4-(4-pyridyl)cyclohexanones and process for preparing them | |
| JPH10204084A (ja) | ３−（３−ピリジルメチルアミノ）−３，４−ジヒドロ−２（１ｈ）−キナゾリノン誘導体の製造方法及び中間体化合物 | |
| JP2958835B2 (ja) | ４−（１−カルボキシアルキル）アゼチジン−２−オン誘導体の製造法 | |
| JP3272170B2 (ja) | ピリジン誘導体の製造法 | |
| JP2880203B2 (ja) | フラノン誘導体の製法 | |
| JPH041746B2 (he) | ||
| EP0564083A1 (en) | Conversion of pyridine-2,3-dicarboxylic acid esters to their cyclic anhydrides | |
| KR900001173B1 (ko) | 2-알콕시카르보닐-4-(4-피리딜)시클로헥사논의 제조방법 | |
| DK162517B (da) | 3-hydroxy-3-(2-methyl-5-pyridyl)-propionsyrealkylestere samt fremgangsmaade til fremstilling deraf | |
| JPS5951534B2 (ja) | ２−アミノ−３−ヒドロキシピリジン誘導体の製造法 |