SU703527A1 - Method of preparing 1-formylcarbazole - Google Patents
Method of preparing 1-formylcarbazoleInfo
- Publication number
- SU703527A1 SU703527A1 SU782563580A SU2563580A SU703527A1 SU 703527 A1 SU703527 A1 SU 703527A1 SU 782563580 A SU782563580 A SU 782563580A SU 2563580 A SU2563580 A SU 2563580A SU 703527 A1 SU703527 A1 SU 703527A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- formylcarbazole
- yield
- preparing
- inert gas
- pyridine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- VMHCBSGWJYTOML-UHFFFAOYSA-N 9h-carbazole-1-carbaldehyde Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C=O VMHCBSGWJYTOML-UHFFFAOYSA-N 0.000 title description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 dicarbonyl carbazole derivative Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Indole Compounds (AREA)
Description
Изобретение относитс к усовершенствованному способу получени 1-форМилкарбазола, который находит применение дл получени полимерных пленок со специальными свойствами - фотохромовые материалы и полупроводники .. В литературе известен способ получени 1-формилкарбазола , заключающийс в том, что дикарбонильное производное карбазола бромируют , на полученный бромид действуют вторичным амином, образовавшеес при этом аминопроизводное восстанавливают литийалюминийгидридом и гидролизуют. Выход 10% 1 Недостатком способа вл етс его многостадийность , труднодоступность исходного соединени и малый выход целевого продукта. Целью изобретени вл етс упрощение процесса и повышение выхода целевого продукта за счет сокращени количества стадий и доступ ности исходных соединений. Поставлениа цель достигаетс описываемым способом получени Ьформилкарбазола, заключающемс в том. Что на. 1-метил-3-(индолил-2)пиридиннййодид общей формулы действуют водно-спиртовым раствором щелочи при температуре 60-80° С. Выход 40-51%. Процесс лучше проводить в атмосфере инертного газа, такого как азот. Предлагаемый способ одностадиен и позвол ет получать целевые продукты с высоким выходом. П р и р 1. 1-Формилкарбазол. Смесь 1 г (0,002 мол ) йодметилата 3-(индoлил-2)-пиpиДИнa , 15 г NaOH, 15 мл Н, О и 75 мл этилового спирта вьщерживают в токе гэота при температуре кипени (80° С) в течение 4 ч, после чего реакционную смесь выливают в воду, выпавший осадок отфильтровывают, промывают водой и перекристаллизовывают из 70%-ного этанола. Выход 0,3 г (51%); т.пл.145НбС (по лит. данным т.пл. 146-146,5С); пюсемикарбазон, т.пл. 246-247° (по лит. данным т.пл. ).The invention relates to an improved method for producing 1-formylcarbazole, which is used to produce polymer films with special properties - photochromic materials and semiconductors. In the literature, a method for producing 1-formylcarbazole is known, which dicarbonyl carbazole derivative is brominated, the secondary amine, the resulting amine derivative, is reduced with lithium aluminum hydride and hydrolyzed. Yield 10% 1 The disadvantage of the method is its multi-stage, inaccessibility of the original compound and the low yield of the target product. The aim of the invention is to simplify the process and increase the yield of the target product by reducing the number of stages and the availability of the starting compounds. The goal is achieved by the described method for the preparation of β-formylcarbazole. What's on. 1-methyl-3- (indolyl-2) pyridine iodide of the general formula is operated with an aqueous-alcoholic solution of alkali at a temperature of 60-80 ° C. Yield 40-51%. The process is best carried out in an atmosphere of inert gas, such as nitrogen. The proposed method is single stage and allows to obtain the desired products in high yield. P p and p 1. 1-Formylcarbazole. A mixture of 1 g (0.002 mol) iodomethyl 3- (indolyl-2) -pyridine, 15 g NaOH, 15 ml H, O and 75 ml of ethyl alcohol is kept in a stream of geota at boiling point (80 ° С) for 4 h, after which the reaction mixture is poured into water, the precipitated precipitate is filtered off, washed with water and recrystallized from 70% ethanol. Yield 0.3 g (51%); mp.145NbS (according to the lit. data, mp 146-146.5C); pyusemicarbazon, so pl. 246-247 ° (according to the literary data of T. pl.).
Пример 2. Опыт провод т в услови х примера 1 при нагревании реакционной смеси до 60° С в течени1в 5 ч без инертного газа и получают, Ьформипкарбазол с выходом 40%.Example 2. The experiment was carried out under the conditions of Example 1 by heating the reaction mixture to 60 ° C for 1 hour without an inert gas and to obtain a form of carbazole in 40% yield.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782563580A SU703527A1 (en) | 1978-01-03 | 1978-01-03 | Method of preparing 1-formylcarbazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782563580A SU703527A1 (en) | 1978-01-03 | 1978-01-03 | Method of preparing 1-formylcarbazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU703527A1 true SU703527A1 (en) | 1979-12-15 |
Family
ID=20741815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782563580A SU703527A1 (en) | 1978-01-03 | 1978-01-03 | Method of preparing 1-formylcarbazole |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU703527A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8030334B2 (en) | 2008-06-27 | 2011-10-04 | Novartis Ag | Organic compounds |
-
1978
- 1978-01-03 SU SU782563580A patent/SU703527A1/en active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8030334B2 (en) | 2008-06-27 | 2011-10-04 | Novartis Ag | Organic compounds |
| US8791141B2 (en) | 2008-06-27 | 2014-07-29 | Novartis Ag | Organic compounds |
| US9242963B2 (en) | 2008-06-27 | 2016-01-26 | Novartis Ag | Organic compounds |
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