CH189984A - Process for the preparation of N-diethylaminoethyl-5-amino-m-phenanthroline. - Google Patents
Process for the preparation of N-diethylaminoethyl-5-amino-m-phenanthroline.Info
- Publication number
- CH189984A CH189984A CH189984DA CH189984A CH 189984 A CH189984 A CH 189984A CH 189984D A CH189984D A CH 189984DA CH 189984 A CH189984 A CH 189984A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenanthroline
- amino
- diethylaminoethyl
- preparation
- ether
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- QOUPJXLLBHPYEV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine;hypochlorous acid Chemical compound ClO.CCN(CC)CCCl QOUPJXLLBHPYEV-UHFFFAOYSA-N 0.000 claims description 3
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical group C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation 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
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von N-Diäthylaminoäthyl-5-amino-m-phenanthrolin. Die Erfindung betrifft ein Verfahren zur Herstellung von N-Diäthylaminoäthyl-5- amino-m-phenanthrolin
EMI0001.0005
welches dadurch gekennzeichnet ist, dass man 5-Amino-m-phenanthrolin mit Diäthylamino- äthylchlorid-chlorhydrat erhitzt.
Das N - Diäthylaminoäthyl - 5 - amino-m- phenanthrolin besitzt schmerzlindernde und bakterizide Eigenschaften und ist deswegen in therapeutischer Hinsicht von Bedeutung. Das nach dem Verfahren gemäss der Erfin- dung hergestellte Produkt ist neu.
Beispiel: 181 g 5-Amino-m-phenanthrolin und 172 g Diäthylaminoäthylchlorid-chlorhydrat wer den nach inniger Mischung in einem Ölbad während 8 Stunden auf ungefähr 170 bis <B>190'</B> C erhitzt. Nach Lösen des Reaktions produktes in Wasser und Abfiltrieren wird das Filtrat alkalisch gemacht.
Das ausfal lende 01 wird in Äther aufgenommen und die ätherische Lösung mit wasserfreier Pottasche getrocknet. Nach dem Abdestillieren des Äthers wird das zurückbleibende 01 der frak tionierten Destillation unterworfen. Im Hoch vakuum geht die Base bei einer Radtempera tur von ungefähr<B>190'</B> C glatt über.
Sie stellt ein zähes, goldgelbes 01 dar. Durch Lösen in trockenem Äther und Ein leiten von Salzsäuregas kann man das orange gefärbte salzsaure Salz erhalten.
Process for the preparation of N-diethylaminoethyl-5-amino-m-phenanthroline. The invention relates to a process for the preparation of N-diethylaminoethyl-5-amino-m-phenanthroline
EMI0001.0005
which is characterized in that 5-amino-m-phenanthroline is heated with diethylamino ethyl chloride chlorohydrate.
The N - diethylaminoethyl - 5 - amino-m-phenanthroline has analgesic and bactericidal properties and is therefore of therapeutic importance. The product manufactured by the method according to the invention is new.
Example: 181 g of 5-amino-m-phenanthroline and 172 g of diethylaminoethyl chloride chlorohydrate are heated to about 170 to 190 ° C for 8 hours after thorough mixing in an oil bath. After the reaction product has been dissolved in water and filtered off, the filtrate is made alkaline.
The precipitating end 01 is taken up in ether and the ethereal solution is dried with anhydrous potash. After the ether has been distilled off, the remaining oil is subjected to fractional distillation. In high vacuum, the base passes over smoothly at a bike temperature of around <B> 190 '</B> C.
It represents a tough, golden yellow 01. The orange-colored hydrochloric acid salt can be obtained by dissolving it in dry ether and introducing hydrochloric acid gas.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL189984X | 1934-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH189984A true CH189984A (en) | 1937-03-31 |
Family
ID=19777813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH189984D CH189984A (en) | 1934-12-22 | 1935-09-02 | Process for the preparation of N-diethylaminoethyl-5-amino-m-phenanthroline. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH189984A (en) |
-
1935
- 1935-09-02 CH CH189984D patent/CH189984A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2310773A1 (en) | NEW QUINOLINESSIC ACID DERIVATIVES AND THE PROCESS FOR THEIR PRODUCTION | |
| CH189984A (en) | Process for the preparation of N-diethylaminoethyl-5-amino-m-phenanthroline. | |
| DE611054C (en) | Process for the preparation of paradiketocamphane carboxylic acid and of ketooxycamphane carboxylic acid | |
| DE809808C (en) | Process for the production of unsaturated aldehydes | |
| DE618213C (en) | Process for the preparation of arylides of 4-oxydiphenyl-3-carboxylic acid | |
| CH194996A (en) | Process for the preparation of N-dimethylaminoethyl-5-amino-m-phenanthroline. | |
| CH218517A (en) | Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-isopropyl-ketone. | |
| CH194997A (en) | Process for the preparation of N- (γ-diethylaminopropyl) -5-amino-m-phenanthroline. | |
| DE889156C (en) | Process for the production of xanthopterins | |
| DE576966C (en) | Process for the preparation of Oxycarbazolcarbonsaeurylamiden | |
| DE582715C (en) | Process for the preparation of 4-butylaminobenzoic acid ª ‰ -dimethylaminoaethyl ester | |
| DE510452C (en) | Process for the preparation of 2,4'-oxyarylaminonaphthalenecarboxylic acids | |
| CH125832A (en) | Process for the preparation of diethylaminoethyl-8-aminoquinoline. | |
| CH120257A (en) | Process for the preparation of a new oxynaphthalene carboxylic acid. | |
| CH207648A (en) | Process for the preparation of a new quaternary ammonium salt. | |
| CH159079A (en) | Process for the preparation of an acridine derivative. | |
| CH190546A (en) | Process for the preparation of 5-benzoylamino-m-phenanthroline. | |
| CH212593A (en) | Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position. | |
| CH189874A (en) | Process for the production of a new condensation product. | |
| CH200910A (en) | Process for the preparation of a nitrogen-containing aromatic aldehyde. | |
| CH154173A (en) | Process for the preparation of 5,6-dimethoxy-8-aminoquinoline. | |
| CH481875A (en) | Process for the preparation of a new amine | |
| CH207656A (en) | Process for the preparation of a new quaternary ammonium salt. | |
| CH194876A (en) | Process for the preparation of 2 (3 ', 5'-Diiodo-2'-B-oxethyl-4'-oxypheny) - 6-iodoquinoline-4-carboxylic acid. | |
| CH240726A (en) | Process for the preparation of a p-amino-benzenesulfonamide. |