SU895287A3 - Способ получени N,N-ди-(с @ -с @ )-алкил-4,4 @ -бипиридиловой соли - Google Patents
Способ получени N,N-ди-(с @ -с @ )-алкил-4,4 @ -бипиридиловой соли Download PDFInfo
- Publication number
- SU895287A3 SU895287A3 SU782595552A SU2595552A SU895287A3 SU 895287 A3 SU895287 A3 SU 895287A3 SU 782595552 A SU782595552 A SU 782595552A SU 2595552 A SU2595552 A SU 2595552A SU 895287 A3 SU895287 A3 SU 895287A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkyl
- water
- bipyridyl
- reaction
- tetrahydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- -1 aromatic nitro compound Chemical class 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 239000008346 aqueous phase Substances 0.000 claims description 18
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 11
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003729 cation exchange resin Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 5
- 239000012071 phase Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- FRYSEKUUHUUJPX-UHFFFAOYSA-N 2-pyridin-2-ylpyridine-4-carboxylic acid Chemical class OC(=O)C1=CC=NC(C=2N=CC=CC=2)=C1 FRYSEKUUHUUJPX-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000006286 aqueous extract Substances 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 238000003809 water extraction Methods 0.000 claims 1
- OWCZSCYFUDVKNC-UHFFFAOYSA-N 4-(1,2,3,4-tetrahydropyridin-4-yl)pyridine Chemical group C1=CNCCC1C1=CC=NC=C1 OWCZSCYFUDVKNC-UHFFFAOYSA-N 0.000 abstract 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 19
- PBYLFGPWFUSZRA-UHFFFAOYSA-N 1-methyl-4-(1-methylpiperidin-4-yl)-2h-pyridine Chemical compound C1CN(C)CCC1C1=CCN(C)C=C1 PBYLFGPWFUSZRA-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 239000011521 glass Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- HZONRRHNQILCNO-UHFFFAOYSA-N 1-methyl-2h-pyridine Chemical class CN1CC=CC=C1 HZONRRHNQILCNO-UHFFFAOYSA-N 0.000 description 5
- 238000006471 dimerization reaction Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- QAIGYXWRIHZZAA-UHFFFAOYSA-M 1-methylpyridin-1-ium;chloride Chemical compound [Cl-].C[N+]1=CC=CC=C1 QAIGYXWRIHZZAA-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- IARCGBCZSPZLGK-UHFFFAOYSA-N 1-methyl-1,2-dihydropyridin-1-ium;chloride Chemical compound Cl.CN1CC=CC=C1 IARCGBCZSPZLGK-UHFFFAOYSA-N 0.000 description 1
- SIYNZLOGCUBUSY-UHFFFAOYSA-N CCN1C=CC=CC1.I Chemical compound CCN1C=CC=CC1.I SIYNZLOGCUBUSY-UHFFFAOYSA-N 0.000 description 1
- PSFDPZJKGCNILV-UHFFFAOYSA-N IC1N(C=CC=C1)C Chemical compound IC1N(C=CC=C1)C PSFDPZJKGCNILV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000008961 swelling Effects 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
- C07D213/22—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 containing two or more pyridine rings directly linked together, e.g. bipyridyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3403777A JPS53127481A (en) | 1977-03-29 | 1977-03-29 | Preparation of n,n'-di-substituted bipyridinium salt |
| JP14885277A JPS5481276A (en) | 1977-12-13 | 1977-12-13 | Preparation of n,n-disubstituted bipyridinium salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU895287A3 true SU895287A3 (ru) | 1981-12-30 |
Family
ID=26372828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782595552A SU895287A3 (ru) | 1977-03-29 | 1978-03-29 | Способ получени N,N-ди-(с @ -с @ )-алкил-4,4 @ -бипиридиловой соли |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4151165A (OSRAM) |
| DE (1) | DE2812730C3 (OSRAM) |
| FR (1) | FR2385700A1 (OSRAM) |
| GB (1) | GB1602523A (OSRAM) |
| SU (1) | SU895287A3 (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5541330A (en) * | 1991-12-10 | 1996-07-30 | Eastman Kodak Company | Ion-sensitive compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1261897A (en) * | 1968-12-20 | 1972-01-26 | Ici Ltd | Manufacture of bipyridylium salts |
| GB1235373A (en) * | 1968-04-08 | 1971-06-16 | Ici Ltd | Production of 1.1'-disubstituted bipyridylium salts |
| GB1257332A (OSRAM) * | 1968-04-16 | 1971-12-15 | ||
| GB1259840A (en) * | 1968-12-23 | 1972-01-12 | Ici Ltd | Manufacture of bipyridylium salts |
-
1978
- 1978-03-23 DE DE2812730A patent/DE2812730C3/de not_active Expired
- 1978-03-23 US US05/889,408 patent/US4151165A/en not_active Expired - Lifetime
- 1978-03-28 FR FR7808974A patent/FR2385700A1/fr active Granted
- 1978-03-29 GB GB12277/78A patent/GB1602523A/en not_active Expired
- 1978-03-29 SU SU782595552A patent/SU895287A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1602523A (en) | 1981-11-11 |
| DE2812730C3 (de) | 1981-03-19 |
| FR2385700B1 (OSRAM) | 1982-11-19 |
| US4151165A (en) | 1979-04-24 |
| FR2385700A1 (fr) | 1978-10-27 |
| DE2812730B2 (de) | 1980-07-03 |
| DE2812730A1 (de) | 1978-10-19 |
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