NO803010L - Fremgangsmaate til fremstilling av 3-(4-pyridinyl) anilin fra 3-(4-pyridinyl)-2-cykloheksen-1-on-oksim. - Google Patents
Fremgangsmaate til fremstilling av 3-(4-pyridinyl) anilin fra 3-(4-pyridinyl)-2-cykloheksen-1-on-oksim.Info
- Publication number
- NO803010L NO803010L NO803010A NO803010A NO803010L NO 803010 L NO803010 L NO 803010L NO 803010 A NO803010 A NO 803010A NO 803010 A NO803010 A NO 803010A NO 803010 L NO803010 L NO 803010L
- Authority
- NO
- Norway
- Prior art keywords
- pyridinyl
- oxime
- acetic anhydride
- aniline
- approx
- Prior art date
Links
- BDSBSHZVSVKIHM-UHFFFAOYSA-N 3-pyridin-4-ylaniline Chemical compound NC1=CC=CC(C=2C=CN=CC=2)=C1 BDSBSHZVSVKIHM-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 4-PYRIDINYL Chemical class 0.000 title description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 26
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 26
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 12
- 150000002923 oximes Chemical class 0.000 claims description 6
- XZJNKMZDJMQHQE-UHFFFAOYSA-N N-(3-pyridin-4-ylcyclohex-2-en-1-ylidene)hydroxylamine Chemical compound ON=C1CCCC(C=2C=CN=CC=2)=C1 XZJNKMZDJMQHQE-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- OPIBZZLCZBMFGN-UHFFFAOYSA-N n-(3-pyridin-4-ylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C=CN=CC=2)=C1 OPIBZZLCZBMFGN-UHFFFAOYSA-N 0.000 claims description 3
- 230000000397 acetylating effect Effects 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- YTVCCNFJGGOBAH-UHFFFAOYSA-N 3-pyridin-4-ylcyclohex-2-en-1-one Chemical compound O=C1CCCC(C=2C=CN=CC=2)=C1 YTVCCNFJGGOBAH-UHFFFAOYSA-N 0.000 description 1
- MNALUTYMBUBKNX-UHFFFAOYSA-N 6-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(OC)=CC=C21 MNALUTYMBUBKNX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 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
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- OKQIEBVRUGLWOR-UHFFFAOYSA-N n-naphthalen-1-ylacetamide Chemical class C1=CC=C2C(NC(=O)C)=CC=CC2=C1 OKQIEBVRUGLWOR-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XBPZXDSZHPDXQU-UHFFFAOYSA-N rosoxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC=C1C1=CC=NC=C1 XBPZXDSZHPDXQU-UHFFFAOYSA-N 0.000 description 1
- 229960003889 rosoxacin Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005292 vacuum distillation 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
-
- 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
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10319179A | 1979-12-13 | 1979-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO803010L true NO803010L (no) | 1981-06-15 |
Family
ID=22293865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO803010A NO803010L (no) | 1979-12-13 | 1980-10-09 | Fremgangsmaate til fremstilling av 3-(4-pyridinyl) anilin fra 3-(4-pyridinyl)-2-cykloheksen-1-on-oksim. |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5687563A (fr) |
| KR (1) | KR830004246A (fr) |
| AR (1) | AR225058A1 (fr) |
| AT (1) | ATA509880A (fr) |
| AU (1) | AU532087B2 (fr) |
| BE (1) | BE885570A (fr) |
| CA (1) | CA1129864A (fr) |
| DE (1) | DE3038778A1 (fr) |
| DK (1) | DK432880A (fr) |
| ES (1) | ES495606A0 (fr) |
| FI (1) | FI803131L (fr) |
| FR (1) | FR2471375A1 (fr) |
| GB (1) | GB2065635A (fr) |
| IL (1) | IL61089A (fr) |
| IT (1) | IT1193982B (fr) |
| LU (1) | LU82843A1 (fr) |
| NL (1) | NL8005661A (fr) |
| NO (1) | NO803010L (fr) |
| NZ (1) | NZ194952A (fr) |
| PT (1) | PT71818B (fr) |
| SE (1) | SE8007188L (fr) |
| ZA (1) | ZA806200B (fr) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4026900A (en) * | 1976-03-19 | 1977-05-31 | Sterling Drug Inc. | 3-(Pyridinyl)-2-cyclohexen-1-ones |
-
1980
- 1980-09-15 NZ NZ194952A patent/NZ194952A/xx unknown
- 1980-09-19 PT PT71818A patent/PT71818B/pt unknown
- 1980-09-19 IL IL61089A patent/IL61089A/xx unknown
- 1980-09-22 AU AU62594/80A patent/AU532087B2/en not_active Ceased
- 1980-09-22 IT IT24826/80A patent/IT1193982B/it active
- 1980-09-30 GB GB8031533A patent/GB2065635A/en not_active Withdrawn
- 1980-10-02 FI FI803131A patent/FI803131L/fi not_active Application Discontinuation
- 1980-10-03 ES ES495606A patent/ES495606A0/es active Granted
- 1980-10-08 ZA ZA00806200A patent/ZA806200B/xx unknown
- 1980-10-08 FR FR8021517A patent/FR2471375A1/fr active Pending
- 1980-10-08 BE BE1/9976A patent/BE885570A/fr not_active IP Right Cessation
- 1980-10-09 JP JP14191380A patent/JPS5687563A/ja active Pending
- 1980-10-09 NO NO803010A patent/NO803010L/no unknown
- 1980-10-13 LU LU82843A patent/LU82843A1/fr unknown
- 1980-10-13 DK DK432880A patent/DK432880A/da not_active Application Discontinuation
- 1980-10-13 KR KR1019800003934A patent/KR830004246A/ko unknown
- 1980-10-14 AT AT0509880A patent/ATA509880A/de not_active Application Discontinuation
- 1980-10-14 AR AR282874A patent/AR225058A1/es active
- 1980-10-14 DE DE19803038778 patent/DE3038778A1/de not_active Withdrawn
- 1980-10-14 NL NL8005661A patent/NL8005661A/nl not_active Application Discontinuation
- 1980-10-14 SE SE8007188A patent/SE8007188L/xx not_active Application Discontinuation
- 1980-12-10 CA CA366,467A patent/CA1129864A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5687563A (en) | 1981-07-16 |
| DE3038778A1 (de) | 1981-06-19 |
| ZA806200B (en) | 1981-09-30 |
| AU532087B2 (en) | 1983-09-15 |
| PT71818A (en) | 1980-10-01 |
| ES8107188A1 (es) | 1981-09-01 |
| SE8007188L (sv) | 1981-06-14 |
| BE885570A (fr) | 1981-04-08 |
| KR830004246A (ko) | 1983-07-09 |
| DK432880A (da) | 1981-06-14 |
| NZ194952A (en) | 1982-09-07 |
| ES495606A0 (es) | 1981-09-01 |
| GB2065635A (en) | 1981-07-01 |
| ATA509880A (de) | 1983-09-15 |
| FI803131L (fi) | 1981-06-14 |
| FR2471375A1 (fr) | 1981-06-19 |
| IT8024826A0 (it) | 1980-09-22 |
| AU6259480A (en) | 1981-06-25 |
| IL61089A0 (en) | 1980-11-30 |
| AR225058A1 (es) | 1982-02-15 |
| IL61089A (en) | 1983-11-30 |
| NL8005661A (nl) | 1981-07-16 |
| IT1193982B (it) | 1988-08-31 |
| PT71818B (en) | 1981-07-07 |
| LU82843A1 (fr) | 1981-06-04 |
| CA1129864A (fr) | 1982-08-17 |
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