SU33237A1 - The method of obtaining 8-quinolazo-2-dynamic pyridines and their derivatives - Google Patents
The method of obtaining 8-quinolazo-2-dynamic pyridines and their derivativesInfo
- Publication number
- SU33237A1 SU33237A1 SU115088A SU115088A SU33237A1 SU 33237 A1 SU33237 A1 SU 33237A1 SU 115088 A SU115088 A SU 115088A SU 115088 A SU115088 A SU 115088A SU 33237 A1 SU33237 A1 SU 33237A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- derivatives
- obtaining
- pyridines
- quinolazo
- dynamic
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 3
- 150000003222 pyridines Chemical class 0.000 title 1
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- -1 8 - quinolyl - azo Chemical group 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- YGGTVPCTAKYCSQ-UHFFFAOYSA-N 6-methoxyquinolin-8-amine Chemical compound N1=CC=CC2=CC(OC)=CC(N)=C21 YGGTVPCTAKYCSQ-UHFFFAOYSA-N 0.000 description 1
- 101100314144 Mus musculus Tnip1 gene Proteins 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- LEMJDBDGPTVGML-UHFFFAOYSA-N [K].ON=O Chemical compound [K].ON=O LEMJDBDGPTVGML-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229940058934 aminoquinoline antimalarials Drugs 0.000 description 1
- 150000005010 aminoquinolines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Description
Предлагаемый способ предусматривает получение 8 - хинолил - азо - 2,6 д амино - пиридин или его производных посредством диазотировани 8амино-хинолина или его замещенных и сочетани полученного диазо-соединени с 2,6,- диамино - пиридином.The proposed method provides for the preparation of 8 - quinolyl - azo - 2.6 d of amino - pyridine or its derivatives by means of diazotization of 8-amino-quinoline or its substituted and combinations of the obtained diazo compound with 2,6, - diamino-pyridine.
Язокрасители из диазоти)рованных анилина, бензидина и 2,6-диаминопиридина получены Д. Е. Чи iи6aбиным и О. Я. Зейде (Журн. Р. Ф. X. О. 1914 г., Jvfo 46, стр. 1234); кроме того Чичибабиным произведены исследовани из области пиридиновых оснований. В патентной литературе же имеютс американские патенты №№ 1680109 и 1680111 на получение арил - азо - 2,6 - диамино - пиридинов и германский патент № 515781 на получение чистого фенил - азо - 2,6 диамино - пиридина монохлорида, оказавшегос бактерицидным и имеющего применение в медицине вследствие слабой довитости.Language dyes from diazotized aniline, benzidine, and 2,6-diaminopyridine were obtained by E. E. Ii and 6 Abin and O. Ya. Zeide (Journal. R. F. Kh. O. 1914, Jvfo 46, p. 1234); In addition, Chichibabin made studies from the field of pyridine bases. In the patent literature, however, there are US patents Nos. 1680109 and 1680111 for obtaining aryl - azo - 2,6 - diamino - pyridines and German patent No. 515781 for obtaining pure phenyl - azo - 2,6 diamino - pyridine monochloride, which turned out to be bactericidal and having in medicine due to poor toxicity.
Авторами насто щего изобретени установлено, что диазртированные аминохинолины и их производные легко сочетаютс в кислом растворе с 2,6 диамйно-пиридином , при чем получаютс хинолил - азо - 2,6 - диамино - пиридины и их производные.The inventors have found that diazrtated aminoquinolines and their derivatives are easily combined in an acidic solution with 2.6 diamido pyridine, resulting in quinolyl azo - 2.6 - diamino - pyridines and their derivatives.
Пример 1. 1,2 г 8-амино-хинолина раствор ют в 15 ну б. см 15% со (48)Example 1. 1.2 g of 8-amino-quinoline is dissolved in 15 b. cm 15% with (48)
л ной кислоты и к охлажденному до 0° раствору приливают при энергичнок перемещивании раств(ЗГ 0,8 г азотистокислого кали в5 см воды. Полученный диазо - раствор ввод т в охлажденный раствор 0,9 г 2,6-диамино- пиридина в бсм 5%-ной сол ной кислоты. После прибавлени уксуснокислого натри , нейтрализации поташем и непродолжительного сто ни выпадает основание кирпично-красного цвета, которое промывают водой и перекристаллизовывают из водного спирта. При этом получаетс вещество с т. пл. 191 -193, трудна растворимое в холодном спирте, в эфире, а также в гор чей и холодной воде. Полученное основание раствор ют в небольшом количестве 10%-ной сол ной кислоты и к теплому раствору приливают равный объем спирта; при сто нии выкристаллизовываетс хлоргидрат красного цвета. Выход почти количественный .lol acid and to the solution cooled to 0 ° is added with a vigorous transfer of the solution (HG 0.8 g of potassium nitrous acid in 5 cm of water. The resulting diazo solution is introduced into a cooled solution of 0.9 g of 2,6-diaminopyridine in BSM 5 After the addition of sodium acetate, neutralization with potash and a short standing, a brick-red base is dropped, which is washed with water and recrystallized from aqueous alcohol, thus obtaining a substance with mp 191 -193, which is difficult to dissolve cold alcohol, on air as well in hot and cold water. The resulting base is dissolved in a small amount of 10% hydrochloric acid and an equal volume of alcohol is added to the warm solution, and the red hydrochloride crystallizes on standing. The yield is almost quantitative.
Пример 2. Краситель из диазотированного 6 - метокси - 8 - аминохинолинэ получаетс путем сочетани с 2,6 диамино - пиридином. Реакци производит-с в услови х, указанных в примере 1. Полученное основание кирпично-красного цвета с т. пл. 108°С трудно растворимо в холодном спирте и эфире, а также в гор чей и в холодной воде.Example 2. A dye from diazotized 6-methoxy-8-aminoquinoline is obtained by combining with 2,6 diamino-pyridine. The reaction is performed under the conditions specified in example 1. The resulting base is brick red in color with mp. 108 ° C is difficult to dissolve in cold alcohol and ether, as well as in hot and cold water.
Предмет изобретени .The subject matter of the invention.
Способ получени 8 -хинолил-азо2 ,6-диамино-пиридина или его производных , отличающийс тем, что 8 аминохинолинThe method of obtaining 8-quinolyl-azo2, 6-diamino-pyridine or its derivatives, characterized in that 8 aminoquinoline
или его замеNH .or replace him.
щенные произвбдные диазотируют и сочетают обычным образом с 2,6 - диамино-пиридином .Schennye products are diazotized and combined in the usual way with 2,6 - diaminopyridine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU115088A SU33237A1 (en) | 1932-09-04 | 1932-09-04 | The method of obtaining 8-quinolazo-2-dynamic pyridines and their derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU115088A SU33237A1 (en) | 1932-09-04 | 1932-09-04 | The method of obtaining 8-quinolazo-2-dynamic pyridines and their derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU33237A1 true SU33237A1 (en) | 1933-11-30 |
Family
ID=48350262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU115088A SU33237A1 (en) | 1932-09-04 | 1932-09-04 | The method of obtaining 8-quinolazo-2-dynamic pyridines and their derivatives |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU33237A1 (en) |
-
1932
- 1932-09-04 SU SU115088A patent/SU33237A1/en active
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