NO803011L - Fremgangsmaate til fremstilling av 3-(4-pyridinyl)-2-cykloheksen-1-oksim. - Google Patents
Fremgangsmaate til fremstilling av 3-(4-pyridinyl)-2-cykloheksen-1-oksim.Info
- Publication number
- NO803011L NO803011L NO803011A NO803011A NO803011L NO 803011 L NO803011 L NO 803011L NO 803011 A NO803011 A NO 803011A NO 803011 A NO803011 A NO 803011A NO 803011 L NO803011 L NO 803011L
- Authority
- NO
- Norway
- Prior art keywords
- pyridinyl
- cyclohexen
- oxime
- oxo
- carbonyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- -1 4-PYRIDINYL Chemical class 0.000 title abstract description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 36
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 20
- 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 claims abstract description 17
- KZAOHLKSKIFDCS-UHFFFAOYSA-N ethyl 5-oxo-2-(pyridine-4-carbonyl)hexanoate Chemical compound CCOC(=O)C(CCC(C)=O)C(=O)C1=CC=NC=C1 KZAOHLKSKIFDCS-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 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 abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 150000002923 oximes Chemical class 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- QOKUDSLTOOMYTB-UHFFFAOYSA-N 1-pyridin-4-ylhexane-1,5-dione Chemical compound CC(=O)CCCC(=O)C1=CC=NC=C1 QOKUDSLTOOMYTB-UHFFFAOYSA-N 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- UCAQDIQSNVAWBD-UHFFFAOYSA-N 5-Oxohexanal Chemical compound CC(=O)CCCC=O UCAQDIQSNVAWBD-UHFFFAOYSA-N 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims 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 abstract description 4
- 229960003889 rosoxacin Drugs 0.000 abstract description 3
- BDSBSHZVSVKIHM-UHFFFAOYSA-N 3-pyridin-4-ylaniline Chemical compound NC1=CC=CC(C=2C=CN=CC=2)=C1 BDSBSHZVSVKIHM-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 239000000284 extract Substances 0.000 abstract description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 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 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum 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
-
- 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
- C07D213/53—Nitrogen atoms
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/105,020 US4246420A (en) | 1979-12-19 | 1979-12-19 | Process for preparing 3-(4-pyridinyl)-2-cyclohene-1-oxime |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO803011L true NO803011L (no) | 1981-06-22 |
Family
ID=22303627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO803011A NO803011L (no) | 1979-12-19 | 1980-10-09 | Fremgangsmaate til fremstilling av 3-(4-pyridinyl)-2-cykloheksen-1-oksim. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4246420A (it) |
| JP (1) | JPS5687564A (it) |
| KR (1) | KR830004248A (it) |
| AR (1) | AR224031A1 (it) |
| AT (1) | AT374182B (it) |
| AU (1) | AU532025B2 (it) |
| BE (1) | BE885571A (it) |
| CA (1) | CA1129865A (it) |
| DE (1) | DE3039143A1 (it) |
| DK (1) | DK436080A (it) |
| ES (1) | ES495967A0 (it) |
| FI (1) | FI803132L (it) |
| FR (1) | FR2471977A1 (it) |
| GB (1) | GB2065636B (it) |
| IL (1) | IL61088A (it) |
| IT (1) | IT1141073B (it) |
| LU (1) | LU82852A1 (it) |
| NL (1) | NL8005660A (it) |
| NO (1) | NO803011L (it) |
| NZ (1) | NZ194951A (it) |
| PT (1) | PT71819B (it) |
| SE (1) | SE8007269L (it) |
| ZA (1) | ZA806201B (it) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109761844B (zh) * | 2019-01-29 | 2021-11-09 | 常州南京大学高新技术研究院 | 一种一锅法制备1-(4-苯甲酰氨基-苯基)-3-苯基丙烷-1,3-二酮的方法 |
Family Cites Families (2)
| 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 |
| US4111946A (en) * | 1976-11-01 | 1978-09-05 | Sterling Drug Inc. | Preparation of 3-(pyridinyl)-2-cyclohexen-1-ones |
-
1979
- 1979-12-19 US US06/105,020 patent/US4246420A/en not_active Expired - Lifetime
-
1980
- 1980-09-15 NZ NZ194951A patent/NZ194951A/xx unknown
- 1980-09-19 PT PT71819A patent/PT71819B/pt unknown
- 1980-09-19 IL IL61088A patent/IL61088A/xx unknown
- 1980-09-22 AU AU62595/80A patent/AU532025B2/en not_active Ceased
- 1980-09-23 IT IT24844/80A patent/IT1141073B/it active
- 1980-09-30 GB GB8031535A patent/GB2065636B/en not_active Expired
- 1980-10-02 FI FI803132A patent/FI803132L/fi not_active Application Discontinuation
- 1980-10-02 AR AR282759A patent/AR224031A1/es active
- 1980-10-08 ZA ZA00806201A patent/ZA806201B/xx unknown
- 1980-10-08 BE BE1/9977A patent/BE885571A/fr not_active IP Right Cessation
- 1980-10-08 FR FR8021518A patent/FR2471977A1/fr active Pending
- 1980-10-09 NO NO803011A patent/NO803011L/no unknown
- 1980-10-14 AT AT0510080A patent/AT374182B/de active
- 1980-10-14 NL NL8005660A patent/NL8005660A/nl not_active Application Discontinuation
- 1980-10-15 LU LU82852A patent/LU82852A1/fr unknown
- 1980-10-15 DK DK436080A patent/DK436080A/da not_active Application Discontinuation
- 1980-10-15 KR KR1019800003962A patent/KR830004248A/ko unknown
- 1980-10-16 DE DE19803039143 patent/DE3039143A1/de not_active Withdrawn
- 1980-10-16 ES ES495967A patent/ES495967A0/es active Granted
- 1980-10-16 SE SE8007269A patent/SE8007269L/xx not_active Application Discontinuation
- 1980-10-16 JP JP14504780A patent/JPS5687564A/ja active Pending
- 1980-12-18 CA CA367,086A patent/CA1129865A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2471977A1 (fr) | 1981-06-26 |
| CA1129865A (en) | 1982-08-17 |
| IL61088A0 (en) | 1980-11-30 |
| FI803132L (fi) | 1981-06-20 |
| IT1141073B (it) | 1986-10-01 |
| US4246420A (en) | 1981-01-20 |
| AR224031A1 (es) | 1981-10-15 |
| BE885571A (fr) | 1981-04-08 |
| ES8107187A1 (es) | 1981-10-01 |
| ATA510080A (de) | 1983-08-15 |
| GB2065636B (en) | 1983-12-14 |
| AU532025B2 (en) | 1983-09-15 |
| IL61088A (en) | 1983-11-30 |
| PT71819A (en) | 1980-10-01 |
| NL8005660A (nl) | 1981-07-16 |
| ZA806201B (en) | 1981-09-30 |
| AT374182B (de) | 1984-03-26 |
| NZ194951A (en) | 1982-11-23 |
| AU6259580A (en) | 1981-06-25 |
| KR830004248A (ko) | 1983-07-09 |
| JPS5687564A (en) | 1981-07-16 |
| ES495967A0 (es) | 1981-10-01 |
| GB2065636A (en) | 1981-07-01 |
| DK436080A (da) | 1981-06-20 |
| DE3039143A1 (de) | 1981-06-25 |
| PT71819B (en) | 1981-07-09 |
| LU82852A1 (fr) | 1981-06-04 |
| SE8007269L (sv) | 1981-06-20 |
| IT8024844A0 (it) | 1980-09-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102436286B1 (ko) | 4-알콕시-3-히드록시피콜린산의 제조 방법 | |
| JPH0123458B2 (it) | ||
| NO803011L (no) | Fremgangsmaate til fremstilling av 3-(4-pyridinyl)-2-cykloheksen-1-oksim. | |
| NO174773B (no) | Fremgangsmåte for fremstilling av chinolonkarboksylsyrer | |
| KR100656636B1 (ko) | 6-메틸-2-(4-메틸-페닐)-이미다조[1,2-ａ]피리딘-3-(Ｎ,Ｎ-디메틸-아세트아미드) 및 중간체의 제조 방법 | |
| JPS6112951B2 (it) | ||
| NO850943L (no) | Fremgangsmaate ved fremstilling av dl-beta-arylaminosyrer | |
| JP2002530282A (ja) | 改良された７−アザインドリル−３−カルボン酸の製造方法 | |
| SU549079A3 (ru) | Способ получени 4-амино-3,5-дигалогенфенилэтаноламинов или их солей | |
| JPH01128982A (ja) | ベンゾ〔ｉｊ〕キノリジン−２−カルボン酸誘導体の合成方法 | |
| NO169006B (no) | Fremgangsmaate ved fremstilling av 6-amino-3-hydrazinopyridazin-derivater | |
| CS261250B2 (en) | Method of 1-methylaminoquinolinecarboxyl acid's and its derivatives production | |
| US4343951A (en) | Method for the preparation of fluoroaniline | |
| JP2561500B2 (ja) | ピリジン−２，３−ジカルボン酸誘導体の製造方法 | |
| WO1991001315A1 (en) | New quinoline derivatives and process for the preparation thereof | |
| NO751054L (it) | ||
| US5625068A (en) | Substituted quinoline herbicide intermediates and process | |
| US4351944A (en) | Improved process for preparing 3-(4-pyridinyl)aniline | |
| NO155196B (no) | Fremgangsmaate ved fremstilling av 4-aminohex-5-en-syre eller et salt derav. | |
| SU372814A1 (ru) | йОЕОиЮЗИАЯ | |
| SU633475A3 (ru) | Способ получени производных пиридина или их солей | |
| KR890002639B1 (ko) | 퀴놀린 유도체의 제조 방법 | |
| NO833422L (no) | Fremgangsmaate for fremstilling av 4(eller 5)-(1-hydroksyalkyl)imidazol-derivater | |
| NO123856B (it) | ||
| AU6072590A (en) | New quinoline derivatives and process for the preparation thereof |