JPS59144759A - ２−クロロニコチン酸の製造方法 - Google Patents
２−クロロニコチン酸の製造方法Info
- Publication number
- JPS59144759A JPS59144759A JP1755683A JP1755683A JPS59144759A JP S59144759 A JPS59144759 A JP S59144759A JP 1755683 A JP1755683 A JP 1755683A JP 1755683 A JP1755683 A JP 1755683A JP S59144759 A JPS59144759 A JP S59144759A
- Authority
- JP
- Japan
- Prior art keywords
- cyanopyridine
- reaction
- oxide
- chloro
- reacting
- 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.)
- Granted
Links
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 title claims description 16
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 39
- JAUPUQRPBNDMDT-UHFFFAOYSA-N 2-chloropyridine-3-carbonitrile Chemical compound ClC1=NC=CC=C1C#N JAUPUQRPBNDMDT-UHFFFAOYSA-N 0.000 claims abstract description 19
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 16
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 5
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 5
- 239000003125 aqueous solvent Substances 0.000 claims abstract description 3
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 21
- 235000005152 nicotinamide Nutrition 0.000 claims description 11
- 239000011570 nicotinamide Substances 0.000 claims description 11
- 229960003966 nicotinamide Drugs 0.000 claims description 5
- USSFUVKEHXDAPM-UHFFFAOYSA-N Nicotinamide N-oxide Chemical compound NC(=O)C1=CC=C[N+]([O-])=C1 USSFUVKEHXDAPM-UHFFFAOYSA-N 0.000 abstract description 9
- 150000003512 tertiary amines Chemical class 0.000 abstract description 5
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 230000000202 analgesic effect Effects 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 40
- 239000013078 crystal Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- FJCFFCXMEXZEIM-UHFFFAOYSA-N oxiniacic acid Chemical compound OC(=O)C1=CC=C[N+]([O-])=C1 FJCFFCXMEXZEIM-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RXTRRIFWCJEMEL-UHFFFAOYSA-N 2-chloropyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1Cl RXTRRIFWCJEMEL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salts Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 150000005480 nicotinamides Chemical class 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical compound O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1755683A JPS59144759A (ja) | 1983-02-07 | 1983-02-07 | ２−クロロニコチン酸の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1755683A JPS59144759A (ja) | 1983-02-07 | 1983-02-07 | ２−クロロニコチン酸の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59144759A true JPS59144759A (ja) | 1984-08-18 |
| JPH0449544B2 JPH0449544B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-08-11 |
Family
ID=11947184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1755683A Granted JPS59144759A (ja) | 1983-02-07 | 1983-02-07 | ２−クロロニコチン酸の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59144759A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4987232A (en) * | 1988-12-05 | 1991-01-22 | Shell Internationale Research Maatschappij, B.V. | Preparation of 2-chloropyridine 3-carboxylic acid esters |
| CN101117332B (zh) | 2006-08-04 | 2012-03-28 | 浙江医药股份有限公司新昌制药厂 | 2-氯烟酸的制备方法 |
| CN103408489A (zh) * | 2013-08-29 | 2013-11-27 | 武穴市永宁医药化工有限公司 | 一种3-氰基吡啶氮氧化物的制备方法 |
| CN103570617A (zh) * | 2013-11-15 | 2014-02-12 | 浙江荣凯化工科技有限公司 | 一种3-氰基-吡啶n-氧化物的制备方法 |
| CN104072409A (zh) * | 2014-06-27 | 2014-10-01 | 温州大学 | 一种吡啶酰胺类化合物的合成方法 |
| CN109438340A (zh) * | 2018-10-25 | 2019-03-08 | 老河口市天和科技有限公司 | 一种2-氯-3-氰基吡啶的制备工艺 |
| CN110790701A (zh) * | 2019-09-29 | 2020-02-14 | 江苏三鹏生物化工有限公司 | 一种利用腈化合物水解制备羧酸的工艺 |
| CN113149903A (zh) * | 2021-04-30 | 2021-07-23 | 安徽国星生物化学有限公司 | 一种氰基吡啶的合成方法及装置 |
| CN116903527A (zh) * | 2023-06-19 | 2023-10-20 | 湖北进创博生物科技有限公司 | 一种基于贵金属纺丝催化布的2-氯烟酸合成方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4867282A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-12-16 | 1973-09-13 | ||
| JPS4880570A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-02-04 | 1973-10-29 | ||
| JPS4881867A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-02-15 | 1973-11-01 | ||
| JPS56169672A (en) * | 1980-06-02 | 1981-12-26 | Koei Chem Co Ltd | Preparation of 2-chloro-3-cyanopyridine and 2- chloronicotinic acid |
-
1983
- 1983-02-07 JP JP1755683A patent/JPS59144759A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4867282A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-12-16 | 1973-09-13 | ||
| JPS4880570A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-02-04 | 1973-10-29 | ||
| JPS4881867A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-02-15 | 1973-11-01 | ||
| JPS56169672A (en) * | 1980-06-02 | 1981-12-26 | Koei Chem Co Ltd | Preparation of 2-chloro-3-cyanopyridine and 2- chloronicotinic acid |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4987232A (en) * | 1988-12-05 | 1991-01-22 | Shell Internationale Research Maatschappij, B.V. | Preparation of 2-chloropyridine 3-carboxylic acid esters |
| CN101117332B (zh) | 2006-08-04 | 2012-03-28 | 浙江医药股份有限公司新昌制药厂 | 2-氯烟酸的制备方法 |
| CN103408489A (zh) * | 2013-08-29 | 2013-11-27 | 武穴市永宁医药化工有限公司 | 一种3-氰基吡啶氮氧化物的制备方法 |
| CN103570617A (zh) * | 2013-11-15 | 2014-02-12 | 浙江荣凯化工科技有限公司 | 一种3-氰基-吡啶n-氧化物的制备方法 |
| CN103570617B (zh) * | 2013-11-15 | 2016-05-04 | 浙江荣凯科技发展股份有限公司 | 一种3-氰基-吡啶n-氧化物的制备方法 |
| CN104072409A (zh) * | 2014-06-27 | 2014-10-01 | 温州大学 | 一种吡啶酰胺类化合物的合成方法 |
| CN109438340A (zh) * | 2018-10-25 | 2019-03-08 | 老河口市天和科技有限公司 | 一种2-氯-3-氰基吡啶的制备工艺 |
| CN110790701A (zh) * | 2019-09-29 | 2020-02-14 | 江苏三鹏生物化工有限公司 | 一种利用腈化合物水解制备羧酸的工艺 |
| CN113149903A (zh) * | 2021-04-30 | 2021-07-23 | 安徽国星生物化学有限公司 | 一种氰基吡啶的合成方法及装置 |
| CN113149903B (zh) * | 2021-04-30 | 2023-02-10 | 安徽国星生物化学有限公司 | 一种氰基吡啶的合成方法及装置 |
| CN116903527A (zh) * | 2023-06-19 | 2023-10-20 | 湖北进创博生物科技有限公司 | 一种基于贵金属纺丝催化布的2-氯烟酸合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0449544B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-08-11 |
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