JPS5827789B2 - 置換ピリジンの製造法 - Google Patents
置換ピリジンの製造法Info
- Publication number
- JPS5827789B2 JPS5827789B2 JP54052562A JP5256279A JPS5827789B2 JP S5827789 B2 JPS5827789 B2 JP S5827789B2 JP 54052562 A JP54052562 A JP 54052562A JP 5256279 A JP5256279 A JP 5256279A JP S5827789 B2 JPS5827789 B2 JP S5827789B2
- Authority
- JP
- Japan
- Prior art keywords
- aldehyde
- compound
- catalyst
- ammonia
- group
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000003222 pyridines Chemical class 0.000 title claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 48
- 239000003054 catalyst Substances 0.000 claims description 25
- 229910021529 ammonia Inorganic materials 0.000 claims description 24
- 150000001299 aldehydes Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- -1 aliphatic oxo compound Chemical class 0.000 claims description 15
- 239000007789 gas Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical group [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 claims 1
- 150000003934 aromatic aldehydes Chemical class 0.000 claims 1
- 238000002203 pretreatment Methods 0.000 claims 1
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 28
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 18
- HJKGBRPNSJADMB-UHFFFAOYSA-N 3-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CN=C1 HJKGBRPNSJADMB-UHFFFAOYSA-N 0.000 description 13
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 229940100595 phenylacetaldehyde Drugs 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- UUCLVSDUMKMBSM-UHFFFAOYSA-N 3-benzylpyridine Chemical compound C=1C=CN=CC=1CC1=CC=CC=C1 UUCLVSDUMKMBSM-UHFFFAOYSA-N 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 3
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- VJBXDBWLDQDBPG-UHFFFAOYSA-N 3-benzyl-4-methylpyridine Chemical compound CC1=CC=NC=C1CC1=CC=CC=C1 VJBXDBWLDQDBPG-UHFFFAOYSA-N 0.000 description 2
- 150000005361 3-phenylpyridines Chemical class 0.000 description 2
- MVTFMJPVPXNIFC-UHFFFAOYSA-N 4-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=CN=CC2=CC=CC=C12 MVTFMJPVPXNIFC-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- MFUVDXOKPBAHMC-UHFFFAOYSA-N magnesium;dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MFUVDXOKPBAHMC-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 2
- JMTCQDNRTSGBGC-UHFFFAOYSA-N 2-(3-methylphenyl)pyridine Chemical compound CC1=CC=CC(C=2N=CC=CC=2)=C1 JMTCQDNRTSGBGC-UHFFFAOYSA-N 0.000 description 1
- JTGKLBDOZYMAEA-UHFFFAOYSA-N 2-thiophen-2-ylacetaldehyde Chemical compound O=CCC1=CC=CS1 JTGKLBDOZYMAEA-UHFFFAOYSA-N 0.000 description 1
- CKCMNYDVHYXJDG-UHFFFAOYSA-N 2-thiophen-3-ylacetaldehyde Chemical compound O=CCC=1C=CSC=1 CKCMNYDVHYXJDG-UHFFFAOYSA-N 0.000 description 1
- 150000003929 3-aminopyridines Chemical class 0.000 description 1
- UCWQMPICSBZRLS-UHFFFAOYSA-N 3-benzyl-5-methylpyridine Chemical compound CC1=CN=CC(CC=2C=CC=CC=2)=C1 UCWQMPICSBZRLS-UHFFFAOYSA-N 0.000 description 1
- QDTQNHLHBKGUBF-UHFFFAOYSA-N 3-thiophen-3-ylpropanal Chemical compound O=CCCC=1C=CSC=1 QDTQNHLHBKGUBF-UHFFFAOYSA-N 0.000 description 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
- RXKHEBJUSZNIQI-UHFFFAOYSA-N 5-benzyl-2-methylpyridine Chemical compound C1=NC(C)=CC=C1CC1=CC=CC=C1 RXKHEBJUSZNIQI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 101000662791 Homo sapiens Trafficking protein particle complex subunit 3 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 102100037494 Trafficking protein particle complex subunit 3 Human genes 0.000 description 1
- ADSXDBCZNVXTRD-UHFFFAOYSA-N [Mg]C1=CC=CC=C1 Chemical class [Mg]C1=CC=CC=C1 ADSXDBCZNVXTRD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical compound [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- LDDQLRUQCUTJBB-UHFFFAOYSA-O azanium;hydrofluoride Chemical compound [NH4+].F LDDQLRUQCUTJBB-UHFFFAOYSA-O 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
- 229940104869 fluorosilicate Drugs 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- JDOZOOBCADNBIJ-UHFFFAOYSA-N lithium;2h-pyridin-2-ide Chemical compound [Li+].C1=CC=N[C-]=C1 JDOZOOBCADNBIJ-UHFFFAOYSA-N 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- HTJPFOOMBUPQDN-UHFFFAOYSA-N pent-1-en-3-one pent-3-en-2-one Chemical class CCC(=O)C=C.CC=CC(C)=O HTJPFOOMBUPQDN-UHFFFAOYSA-N 0.000 description 1
- RYMBAPVTUHZCNF-UHFFFAOYSA-N phenyl(pyridin-3-yl)methanone Chemical compound C=1C=CN=CC=1C(=O)C1=CC=CC=C1 RYMBAPVTUHZCNF-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- KKWVSVIYNHRKPT-UHFFFAOYSA-N pyridine-3-carbonyl pyridine-3-carboperoxoate Chemical compound C=1C=CN=CC=1C(=O)OOC(=O)C1=CC=CN=C1 KKWVSVIYNHRKPT-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
- C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
- C07D213/12—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from unsaturated compounds
-
- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782819196 DE2819196A1 (de) | 1978-05-02 | 1978-05-02 | Verfahren zur herstellung substituierter pyridine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54144379A JPS54144379A (en) | 1979-11-10 |
| JPS5827789B2 true JPS5827789B2 (ja) | 1983-06-11 |
Family
ID=6038491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54052562A Expired JPS5827789B2 (ja) | 1978-05-02 | 1979-05-01 | 置換ピリジンの製造法 |
Country Status (11)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3741159A1 (de) * | 1987-12-04 | 1989-06-15 | Basf Ag | Verfahren zur herstellung von cyano-pyridinen |
| US6492524B1 (en) * | 2001-03-27 | 2002-12-10 | Council Of Scientific And Industrial Research | Process for the synthesis of an aryl pyridine base using a zeolite catalyst |
| ATE482196T1 (de) * | 2001-03-30 | 2010-10-15 | Council Scient Ind Res | Verfahren zur herstellung von aryl-pyridinyl- derivaten unter verwendung von einem zeolith- katalysator |
| JP4119114B2 (ja) | 2001-11-28 | 2008-07-16 | 広栄化学工業株式会社 | 新規なジヒドロキシ（３−ピリジル）ボラン類 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2554946A1 (de) * | 1975-12-06 | 1977-06-23 | Degussa | Verfahren zur gewinnung von pyridin und 3-methylpyridin |
| DE2639701A1 (de) * | 1976-09-03 | 1978-03-09 | Degussa | Verfahren zur herstellung substituierter pyridine |
-
1978
- 1978-05-02 DE DE19782819196 patent/DE2819196A1/de active Granted
-
1979
- 1979-03-06 NL NL7901788A patent/NL7901788A/xx unknown
- 1979-03-28 FR FR7907835A patent/FR2424911A1/fr active Granted
- 1979-04-11 BR BR7902274A patent/BR7902274A/pt unknown
- 1979-04-13 IL IL57069A patent/IL57069A/xx unknown
- 1979-04-25 GB GB7914375A patent/GB2020270B/en not_active Expired
- 1979-04-26 BE BE0/194856A patent/BE875878A/xx not_active IP Right Cessation
- 1979-04-30 IT IT48890/79A patent/IT1162485B/it active
- 1979-05-01 CA CA326,706A patent/CA1122986A/en not_active Expired
- 1979-05-01 JP JP54052562A patent/JPS5827789B2/ja not_active Expired
- 1979-05-01 CH CH407479A patent/CH638786A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1122986A (en) | 1982-05-04 |
| FR2424911A1 (fr) | 1979-11-30 |
| DE2819196A1 (de) | 1979-11-15 |
| FR2424911B1 (enrdf_load_stackoverflow) | 1984-05-18 |
| IL57069A (en) | 1982-08-31 |
| IL57069A0 (en) | 1979-07-25 |
| BR7902274A (pt) | 1979-12-11 |
| JPS54144379A (en) | 1979-11-10 |
| DE2819196C2 (enrdf_load_stackoverflow) | 1989-03-16 |
| IT1162485B (it) | 1987-04-01 |
| IT7948890A0 (it) | 1979-04-30 |
| CH638786A5 (de) | 1983-10-14 |
| BE875878A (fr) | 1979-10-26 |
| NL7901788A (nl) | 1979-11-06 |
| GB2020270B (en) | 1983-02-02 |
| GB2020270A (en) | 1979-11-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0699397B2 (ja) | ３−メチルピリジン及び３−メチルピペリジンの混合物からの３−シアノピリジンの製造方法 | |
| CA1085850A (en) | Producing pyridines aromatically or heteroaromatically substituted in the 2 position | |
| JP5173897B2 (ja) | アセトニトリルの製造方法 | |
| JPS5827789B2 (ja) | 置換ピリジンの製造法 | |
| US2807618A (en) | Synthesis of pyridine and 3-picoline | |
| US4570021A (en) | Preparation of ketones | |
| JPS62129236A (ja) | メチルイソプロピルケトン及びジエチルケトンの製法 | |
| US2744904A (en) | Process of preparing pyridine and 3-picoline | |
| JPS639495B2 (enrdf_load_stackoverflow) | ||
| JPS5827788B2 (ja) | 置換ピリジンの製法 | |
| US2399361A (en) | Manufacture of cyanogen | |
| JPS6021981B2 (ja) | シアノピリジン類の製造法 | |
| JPS6256141B2 (enrdf_load_stackoverflow) | ||
| US3020281A (en) | Method of preparing quinoline | |
| JP4040471B2 (ja) | ２，３，５−トリメチルピリジン、２，３，６−トリメチルピリジン及び２，３，５，６−テトラメチルピリジンの製造方法 | |
| US5214162A (en) | Process for manufacturing 5-cyano-4-lower alkyloxazoles | |
| JPH03220166A (ja) | α，β―不飽和ニトリルの製造方法 | |
| JPS6313988B2 (enrdf_load_stackoverflow) | ||
| JPS5910662B2 (ja) | 置換ピリジンの製法 | |
| US5075486A (en) | Process for preparing di-n-propylacetonitrile | |
| US3020280A (en) | Quinoline synthesis | |
| US4243612A (en) | Benzylic oxidation process | |
| JPS6130667B2 (enrdf_load_stackoverflow) | ||
| JPS60100558A (ja) | ピリミジンの製造法 | |
| JPS6232189B2 (enrdf_load_stackoverflow) |