DK141528B - Fremgangsmåde til fremstilling af 2-(2-aminobenzoyl)-pyridiner. - Google Patents
Fremgangsmåde til fremstilling af 2-(2-aminobenzoyl)-pyridiner. Download PDFInfo
- Publication number
- DK141528B DK141528B DK576672AA DK576672A DK141528B DK 141528 B DK141528 B DK 141528B DK 576672A A DK576672A A DK 576672AA DK 576672 A DK576672 A DK 576672A DK 141528 B DK141528 B DK 141528B
- Authority
- DK
- Denmark
- Prior art keywords
- solution
- added
- reaction
- aminobenzoyl
- stirred
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 9
- WEWXXYDHYCDEKY-UHFFFAOYSA-N (2-aminophenyl)-pyridin-2-ylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=N1 WEWXXYDHYCDEKY-UHFFFAOYSA-N 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- JDOZOOBCADNBIJ-UHFFFAOYSA-N lithium;2h-pyridin-2-ide Chemical compound [Li+].C1=CC=N[C-]=C1 JDOZOOBCADNBIJ-UHFFFAOYSA-N 0.000 description 8
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- OATYCBHROMXWJO-UHFFFAOYSA-N 2-amino-5-bromobenzonitrile Chemical compound NC1=CC=C(Br)C=C1C#N OATYCBHROMXWJO-UHFFFAOYSA-N 0.000 description 5
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002900 organolithium compounds Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- KHVZPFKJBLTYCC-UHFFFAOYSA-N (2-amino-5-bromophenyl)-pyridin-2-ylmethanone Chemical compound NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 KHVZPFKJBLTYCC-UHFFFAOYSA-N 0.000 description 2
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- XXYUFPQOHIDEQU-UHFFFAOYSA-N 5-pyridin-2-yl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical class C12=CC=CC=C2NC(=O)CN=C1C1=CC=CC=N1 XXYUFPQOHIDEQU-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- -1 ara compound Chemical class 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- LJWKFGGDMBPPAZ-UHFFFAOYSA-N ethoxyethane;toluene Chemical compound CCOCC.CC1=CC=CC=C1 LJWKFGGDMBPPAZ-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- GTDQGKWDWVUKTI-UHFFFAOYSA-N o-aminoacetophenone Chemical compound CC(=O)C1=CC=CC=C1N GTDQGKWDWVUKTI-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent 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
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20062071A | 1971-11-19 | 1971-11-19 | |
| US20062071 | 1971-11-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141528B true DK141528B (da) | 1980-04-14 |
| DK141528C DK141528C (en:Method) | 1980-09-08 |
Family
ID=22742473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK576672AA DK141528B (da) | 1971-11-19 | 1972-11-17 | Fremgangsmåde til fremstilling af 2-(2-aminobenzoyl)-pyridiner. |
Country Status (16)
| Country | Link |
|---|---|
| JP (2) | JPS537432B2 (en:Method) |
| AR (1) | AR195889A1 (en:Method) |
| AT (1) | AT324332B (en:Method) |
| AU (1) | AU470104B2 (en:Method) |
| BE (1) | BE791500A (en:Method) |
| CA (1) | CA971967A (en:Method) |
| CH (1) | CH574929A5 (en:Method) |
| DE (1) | DE2256614C3 (en:Method) |
| DK (1) | DK141528B (en:Method) |
| ES (1) | ES408746A1 (en:Method) |
| FR (1) | FR2160589B1 (en:Method) |
| GB (1) | GB1364157A (en:Method) |
| HU (1) | HU168523B (en:Method) |
| NL (1) | NL155255B (en:Method) |
| SE (1) | SE411623B (en:Method) |
| ZA (1) | ZA727666B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5481264A (en) * | 1977-12-08 | 1979-06-28 | Sagami Chem Res Center | Preparation of 1-methyl-5-aroylpryrrole-2-acetic acid |
| WO2000048997A1 (en) | 1999-02-16 | 2000-08-24 | Kaneka Corporation | SUBSTITUTED ACETYLPYRIDINE DERIVATIVES AND PROCESS FOR THE PREPARATION OF INTERMEDIATES FOR OPTICALLY ACTIVE β3 AGONIST BY THE USE OF THE SAME |
| CN115322144B (zh) * | 2022-08-30 | 2024-05-24 | 上海药坦药物研究开发有限公司 | 一种2-(2-氨基-5-溴-苯甲酰基)吡啶的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3182067A (en) * | 1964-04-09 | 1965-05-04 | Hoffmann La Roche | Benzodiazepine compounds |
-
0
- BE BE791500D patent/BE791500A/xx not_active IP Right Cessation
-
1972
- 1972-10-27 ZA ZA727666A patent/ZA727666B/xx unknown
- 1972-10-30 CH CH1580772A patent/CH574929A5/xx not_active IP Right Cessation
- 1972-11-17 DK DK576672AA patent/DK141528B/da not_active IP Right Cessation
- 1972-11-17 JP JP11488972A patent/JPS537432B2/ja not_active Expired
- 1972-11-17 SE SE7215025A patent/SE411623B/xx unknown
- 1972-11-17 DE DE2256614A patent/DE2256614C3/de not_active Expired
- 1972-11-17 NL NL727215588A patent/NL155255B/xx not_active IP Right Cessation
- 1972-11-17 AT AT980472A patent/AT324332B/de not_active IP Right Cessation
- 1972-11-17 FR FR7240879A patent/FR2160589B1/fr not_active Expired
- 1972-11-17 AU AU49014/72A patent/AU470104B2/en not_active Expired
- 1972-11-17 CA CA156,793A patent/CA971967A/en not_active Expired
- 1972-11-17 HU HUHO1526A patent/HU168523B/hu unknown
- 1972-11-17 GB GB5321372A patent/GB1364157A/en not_active Expired
- 1972-11-18 ES ES72408746A patent/ES408746A1/es not_active Expired
- 1972-11-20 AR AR245206A patent/AR195889A1/es active
-
1977
- 1977-08-10 JP JP52095942A patent/JPS604816B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1364157A (en) | 1974-08-21 |
| JPS4896591A (en:Method) | 1973-12-10 |
| BE791500A (fr) | 1973-05-17 |
| SE411623B (sv) | 1980-01-21 |
| JPS537432B2 (en:Method) | 1978-03-17 |
| CA971967A (en) | 1975-07-29 |
| NL7215588A (en:Method) | 1973-05-22 |
| JPS5387361A (en) | 1978-08-01 |
| DE2256614B2 (de) | 1978-06-01 |
| AT324332B (de) | 1975-08-25 |
| AR195889A1 (es) | 1973-11-15 |
| HU168523B (en:Method) | 1976-05-28 |
| AU4901472A (en) | 1974-05-23 |
| NL155255B (nl) | 1977-12-15 |
| DE2256614A1 (de) | 1973-05-24 |
| DK141528C (en:Method) | 1980-09-08 |
| DE2256614C3 (de) | 1979-02-22 |
| FR2160589B1 (en:Method) | 1978-02-10 |
| ES408746A1 (es) | 1976-04-01 |
| JPS604816B2 (ja) | 1985-02-06 |
| ZA727666B (en) | 1973-06-27 |
| AU470104B2 (en) | 1976-03-04 |
| CH574929A5 (en:Method) | 1976-04-30 |
| FR2160589A1 (en:Method) | 1973-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |