NO801549L - Fremgangsmaate for fremstilling av pyrrolinderivater - Google Patents
Fremgangsmaate for fremstilling av pyrrolinderivaterInfo
- Publication number
- NO801549L NO801549L NO801549A NO801549A NO801549L NO 801549 L NO801549 L NO 801549L NO 801549 A NO801549 A NO 801549A NO 801549 A NO801549 A NO 801549A NO 801549 L NO801549 L NO 801549L
- Authority
- NO
- Norway
- Prior art keywords
- dialkyl
- pyrroline
- formyl
- reaction
- sulfuric acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title description 5
- 150000003236 pyrrolines Chemical class 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 14
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 11
- KQCAARBOQRQIKO-UHFFFAOYSA-N 2,2,4,5,5-pentamethyl-1h-pyrrole-3-carbaldehyde Chemical compound CC1=C(C=O)C(C)(C)NC1(C)C KQCAARBOQRQIKO-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229940101209 mercuric oxide Drugs 0.000 claims description 3
- 229940100892 mercury compound Drugs 0.000 claims description 2
- 150000002731 mercury compounds Chemical class 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000001361 allenes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000002730 mercury Chemical class 0.000 description 2
- 229910000474 mercury oxide Inorganic materials 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KYDCJAGSMNFHPT-UHFFFAOYSA-N (2,2,4,5,5-pentamethylpyrrolidin-3-yl)methanol Chemical compound CC1C(CO)C(C)(C)NC1(C)C KYDCJAGSMNFHPT-UHFFFAOYSA-N 0.000 description 1
- YUPVAJWWKRYZCW-UHFFFAOYSA-N 2,2,4,5,5-pentamethylpyrrolidine-3-carbaldehyde Chemical compound CC1C(C=O)C(C)(C)NC1(C)C YUPVAJWWKRYZCW-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- BNDRWEVUODOUDW-UHFFFAOYSA-N 3-Hydroxy-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)O BNDRWEVUODOUDW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23080/79A IT1121521B (it) | 1979-05-29 | 1979-05-29 | Processo per la preparazione di 2,2-dialchil-4 metil-5,5 dialchil-3 formil-3 pirrolina e prodotti cosi'ottenuti |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO801549L true NO801549L (no) | 1980-12-01 |
Family
ID=11203554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO801549A NO801549L (no) | 1979-05-29 | 1980-05-23 | Fremgangsmaate for fremstilling av pyrrolinderivater |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4393218A (ru) |
| JP (1) | JPS55160759A (ru) |
| AT (1) | AT373872B (ru) |
| BE (1) | BE883535A (ru) |
| CA (1) | CA1138880A (ru) |
| CH (1) | CH649286A5 (ru) |
| CS (1) | CS215061B2 (ru) |
| DD (1) | DD151161A5 (ru) |
| DE (1) | DE3020298C2 (ru) |
| DK (1) | DK212080A (ru) |
| FR (1) | FR2457857A1 (ru) |
| GB (1) | GB2051058B (ru) |
| IT (1) | IT1121521B (ru) |
| NL (1) | NL8003128A (ru) |
| NO (1) | NO801549L (ru) |
| SU (1) | SU955858A3 (ru) |
| ZA (1) | ZA803133B (ru) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1151734B (it) * | 1982-04-22 | 1986-12-24 | Anic Spa | Processo per la preparazione di 1,1,3,3 tetrametil-2,3 diidro-1-h-isoindoli sostituiti in posizione 5 e/o 6 e prodotti cosi' ottenuti |
| IT1196327B (it) * | 1984-11-16 | 1988-11-16 | Consiglio Nazionale Ricerche | 3-aza-7-idrossi-2,2,4,4-tetraalchilbiciclo (3.3.0) ottani,procedimento per la loro preparazione,intermedi adatti allo scopo e procedimento per l'ottenimento di questi ultimi |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1468046A (en) * | 1975-05-22 | 1977-03-23 | Ici Ltd | Production of sterically hindered 5-membered heterocyclic rings containing nitrogen |
-
1979
- 1979-05-29 IT IT23080/79A patent/IT1121521B/it active
-
1980
- 1980-05-08 CA CA000351516A patent/CA1138880A/en not_active Expired
- 1980-05-14 DK DK212080A patent/DK212080A/da not_active Application Discontinuation
- 1980-05-16 GB GB8016258A patent/GB2051058B/en not_active Expired
- 1980-05-16 AT AT0263480A patent/AT373872B/de not_active IP Right Cessation
- 1980-05-20 CH CH3929/80A patent/CH649286A5/it not_active IP Right Cessation
- 1980-05-23 NO NO801549A patent/NO801549L/no unknown
- 1980-05-26 ZA ZA00803133A patent/ZA803133B/xx unknown
- 1980-05-27 FR FR8011731A patent/FR2457857A1/fr active Granted
- 1980-05-28 SU SU802926553A patent/SU955858A3/ru active
- 1980-05-28 JP JP7021880A patent/JPS55160759A/ja active Pending
- 1980-05-28 CS CS803746A patent/CS215061B2/cs unknown
- 1980-05-28 DE DE3020298A patent/DE3020298C2/de not_active Expired
- 1980-05-29 BE BE0/200808A patent/BE883535A/fr not_active IP Right Cessation
- 1980-05-29 NL NL8003128A patent/NL8003128A/nl not_active Application Discontinuation
- 1980-05-29 DD DD80221450A patent/DD151161A5/de unknown
-
1981
- 1981-12-07 US US06/327,753 patent/US4393218A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA1138880A (en) | 1983-01-04 |
| DE3020298A1 (de) | 1980-12-04 |
| CS215061B2 (en) | 1982-07-30 |
| BE883535A (fr) | 1980-12-01 |
| ATA263480A (de) | 1983-07-15 |
| FR2457857A1 (fr) | 1980-12-26 |
| NL8003128A (nl) | 1980-12-02 |
| JPS55160759A (en) | 1980-12-13 |
| AT373872B (de) | 1984-02-27 |
| IT7923080A0 (it) | 1979-05-29 |
| GB2051058B (en) | 1983-03-16 |
| FR2457857B1 (ru) | 1983-04-22 |
| DD151161A5 (de) | 1981-10-08 |
| SU955858A3 (ru) | 1982-08-30 |
| ZA803133B (en) | 1981-05-27 |
| DK212080A (da) | 1980-11-30 |
| CH649286A5 (it) | 1985-05-15 |
| US4393218A (en) | 1983-07-12 |
| GB2051058A (en) | 1981-01-14 |
| IT1121521B (it) | 1986-04-02 |
| DE3020298C2 (de) | 1983-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR960000758B1 (ko) | 광학적 활성 히드록시벤질아민 유도체 및 그의 제조방법 | |
| US5663441A (en) | Production of mono-N-alkyl-dinitroalkylanilines and N-alkyl-dinitroaniline derivatives | |
| Hauser et al. | Alkylation of Diphenylmethane with Alkyl Halides by Sodium Amide. Substitution versus β-Elimination. Relative Acidities of Diphenylmethane and Ammonia | |
| US4067905A (en) | Preparation of 2-amino-n-butanol | |
| NO801549L (no) | Fremgangsmaate for fremstilling av pyrrolinderivater | |
| US5910591A (en) | Method of preparation of 4-hydroxy-1,2,2,6,6-pentamethylpiperidine | |
| US4960938A (en) | Preparing 2-chlorobenzylamine from 2-chlorobenzylchloride via 2-chlorobenzylphthalimide | |
| EP0169602B1 (en) | Preparation of n-substituted azetidine 3-carboxylic acid derivatives | |
| BG64948B1 (bg) | Метод за получаване на полихалогенирани паратрифлуорометиланилини | |
| US4010160A (en) | Process for the manufacture of 1,3-bis-(β-ethylhexyl)-5-amino-5-methyl-hexahydropyrimidine | |
| CA1323878C (en) | Process for synthesis of azetidine and novel intermediates therefor | |
| US4469876A (en) | Process for the production of L-proline | |
| US3137729A (en) | Products from the reaction of alkynes and secondary amines | |
| US4966979A (en) | Process for synthesis of azetidine and novel intermediates therefor | |
| CA1130290A (en) | Method for preparing 7,8-dichloro-tetrahydroisoquinoline | |
| US4065450A (en) | Process for preparing 2-guanidinomethyl-perhydroazocine-sulfate | |
| US4376860A (en) | Pyridyl ketone | |
| US4048169A (en) | 1,3-Bis-(β-ethylhexyl)-5-nitro-5-methyl-hexahydropyrimidine-naphthalene-1,5-disulphonate | |
| Murray et al. | Polycyclic azetidines. I. The preparation of benzo [c]‐cis‐6‐azabicyclo [3.2. 0] heptane | |
| US4987266A (en) | Process for the manufacture of nitrophenetole | |
| KR830001500B1 (ko) | 7.8 디클로로 테트라하이드로 이소퀴놀린의 제조방법 | |
| KR820001121B1 (ko) | 2-아미노메틸 피롤리딘의 제법 | |
| JPS6075462A (ja) | Ν−アルキルデカヒドロイソキノリンの製造方法 | |
| JPH01175948A (ja) | ３，５‐ジクロロフェノールの製造方法 | |
| EP0194554A2 (en) | Process for production of oxime derivatives |