SU958422A1 - Process for producing 3(5)-(indolyl-3)pyrazole - Google Patents
Process for producing 3(5)-(indolyl-3)pyrazole Download PDFInfo
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- SU958422A1 SU958422A1 SU803210642A SU3210642A SU958422A1 SU 958422 A1 SU958422 A1 SU 958422A1 SU 803210642 A SU803210642 A SU 803210642A SU 3210642 A SU3210642 A SU 3210642A SU 958422 A1 SU958422 A1 SU 958422A1
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- USSR - Soviet Union
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- indolyl
- pyrazole
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- product
- yield
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- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ 3 (5)-(ИНДОЛИЛ-3)-ПИРАЗОЛА(54) METHOD OF OBTAINING 3 (5) - (INDOLYL-3) -PYRAZOL
. 1 . one
Изобретение относитс к способу нолучени 3 (5)-(нндопил-3)-пиразола, который вл етс высокоэффективным протнвовоспали° тельным средством.The invention relates to a method for obtaining 3 (5) - (nndopyl-3) -pyrazole, which is a highly effective anti-inflammatory agent.
Известны 2 споеоба получени 3(5)-(индо Л1ю-3 )-пиразола. .There are 2 known ways to obtain 3 (5) - (Indo L1y-3) -pyrazole. .
Первый способ 1 заключаетс во взаимодействии 3-ацетилиндола (1) с диэтнлоксалатом (11) с образованием дикетоэфира (Ml), который далее реакцией с гидразингидратом переводитс в зтиловый зфир 5-(индолил-3)-пиразол-3-карбоновой кислоты (IV). Эфир IV далее подвергаетс гидролизу до кислоты (V), которую декарбоксилируют в присутствии медно-хромового катализатора, целевой продукт (VI)., .The first method 1 consists in the interaction of 3-acetylindole (1) with diethnloxalate (11) to form the diketoester (Ml), which is then converted by reaction with hydrazine hydrate to ethyl 2-indolyl-3-pyrazole-3-carboxylic acid (IV) . Ether IV is then hydrolyzed to acid (V), which is decarboxylated in the presence of a copper-chromium catalyst, the target product (VI).,.
Второй известный способ получени 2(5)- (индолил-3)-пиразола 2 основан на бромировании Д-(1-ацетил-индолил-3)-акрилового альдегида (Vll) до 2-бррмпрОизводного (VIII), из которого действием гидразингидрата получен целевой 3 (5)-(индолил-3)-пиразол (VI).The second known method for the preparation of 2 (5) - (indolyl-3) -pyrazole 2 is based on brominating D- (1-acetyl-indolyl-3) -acrylic aldehyde (Vll) to 2-bromo-derivative (VIII), from which the hydrazine hydrate is obtained target 3 (5) - (indolyl-3) -pyrazole (VI).
Оба эти способа имеют следующие недостатки: они многостадийнь и трудоемки вBoth of these methods have the following disadvantages: they are multistage and laborious in
экспериментальн(ж оформлении; требуют труднодоступных исходных реагентов, которые в свою очередь получаютс в результате слож ( реакций; многие стадии идут с низкими выходами в присутствии труднодоступных катализаторов; выделение целевого продукта очень трудоемко; выход продукта очень мал, учитыва выходы на промеж)гточных стади х от 30 до 40%.experimental (design; require inaccessible initial reagents, which in turn are obtained as a result of complex (reactions; many stages go with low yields in the presence of hardly accessible catalysts; isolation of the target product is very laborious; yield of the product is very small, taking into account yields in between) x from 30 to 40%.
Цель изобретени - упрощение процесса и The purpose of the invention is to simplify the process and
10 уведшчение выхода целевого продукта.10 increase in the yield of the target product.
Поставленна цель достигаетс тем, что согласно способу получени 3(5)-(индолнл-3)-пиразола с использованием гидразингидрата йодметилат 4 (индолш1-3)-пирнмидина подвер15 гают взаимодействию с гидразингидратом в среде этанола при температуре кипени .This goal is achieved by the method of preparing 3 (5) - (indoln-3) -pyrazole using iodomethyl 4 (indolch-1-3) -pyrmidine hydrazine hydrazine to react with hydrazine hydrate in ethanol at boiling point.
Вь1ход 89%.Incidence of 89%.
Пример. 3(5)-(шздолил-3)-1шразол , (VI). Смесь 1,7 г (0,005 моль) йодметилата Example. 3 (5) - (shzdolil-3) -1shrazol, (VI). A mixture of 1.7 g (0.005 mol) iodomethyl
20 4-(индолил-З)-пиримидина в 10 мл этанола . выдерживают при температуре кипени 1 ч. Реакционную смесь разбавл ют водой, экстрагируют хлороформом, хлороформные выт жк 20 4- (indolyl-3) -pyrimidine in 10 ml of ethanol. kept at boiling point for 1 h. The reaction mixture is diluted with water, extracted with chloroform, chloroform extracts
3 9584223 958422
сушат над KiCOj, хлороформ отгон ют, а остаток перекристаллизовывают из бензола. Выход 0,8 г (89%). Т. пл. 1ба-16ГС (из беизола ); Rf 02. ИК спектр 11 3320 (N-H); 3200 (N-H).5dried over KiCOj, chloroform was distilled off, and the residue was recrystallized from benzene. Yield 0.8 g (89%). T. pl. 1ba-16GS (from beizol); Rf 02. IR spectrum 11 3320 (N-H); 3200 (N-H) .5
Найдено, %: С 72,3; Н 5,4; N 22,7Found,%: C 72.3; H 5.4; N 22.7
СцНдМзStsNdMz
Вычислено, %: С 71,2; Н 4,9; N 22,9.Calculated,%: C 71.2; H 4.9; N 22.9.
Предлагаемый способ имеет следующие преимущества перед известным: дл получени левого продукта используют доступный реагентйодметилат 4-(индол1ш 3)-пирим дина; реакци протекает,в oufty стадию при очень простом оформлении; целевой продукт получаетс с высоким выходом; вьвделение продукта отли- чаетс простотой.The proposed method has the following advantages over the known one: for the preparation of the left product, the available reagent is 4- (indole-3) pyrim dine; the reaction proceeds, to the oufty stage with a very simple design; target product is obtained in high yield; Product introduction is distinguished by simplicity.
:.-.- /- . : -«.i:.-.- / -. : - ". I
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU803210642A SU958422A1 (en) | 1980-12-02 | 1980-12-02 | Process for producing 3(5)-(indolyl-3)pyrazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU803210642A SU958422A1 (en) | 1980-12-02 | 1980-12-02 | Process for producing 3(5)-(indolyl-3)pyrazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU958422A1 true SU958422A1 (en) | 1982-09-15 |
Family
ID=20929209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU803210642A SU958422A1 (en) | 1980-12-02 | 1980-12-02 | Process for producing 3(5)-(indolyl-3)pyrazole |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU958422A1 (en) |
-
1980
- 1980-12-02 SU SU803210642A patent/SU958422A1/en active
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