CH158148A - Process for the preparation of an acridine derivative. - Google Patents
Process for the preparation of an acridine derivative.Info
- Publication number
- CH158148A CH158148A CH158148DA CH158148A CH 158148 A CH158148 A CH 158148A CH 158148D A CH158148D A CH 158148DA CH 158148 A CH158148 A CH 158148A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- diethylamino
- alcohol
- yellow
- acridine derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- AYTQPRSVTNMLIV-UHFFFAOYSA-N 3,9-dichloroacridine Chemical compound C1=CC=CC2=NC3=CC(Cl)=CC=C3C(Cl)=C21 AYTQPRSVTNMLIV-UHFFFAOYSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001251 acridines Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- OHHIBZKYXJDQEU-UHFFFAOYSA-N 3-chloro-n-phenylaniline Chemical compound ClC1=CC=CC(NC=2C=CC=CC=2)=C1 OHHIBZKYXJDQEU-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- -1 aliphatic diamine Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000010438 heat treatment 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Terfahren zur Darstellung eines Aeridinderivates. (4egenstand vorliegender Erfindung ist ein Verfahren zur Darstellung des bisher noch nicht bekannten 6-Chlor-9-(a-Diäthylamino-8- pentylamino)-aeridins, das als Heilmittel Ver wendung finden soll.
Es ist dadurch gekennzeichnet, dass man auf<B>1</B> Mol 6,9-Dichloracridin <B>1</B> Mol a-Diäthyl- amino-O'-ainiiiopentan einwirken lässt.
<I>Beispiel:</I> 24,8 gr 6,9-Dichloracridin werden im sie denden Wasserbade mit<B>125</B> gr Phenol zu sammengeschmolzen und zur Schmelze<B>17</B> gr a-Diäthylamino-8-aminopentan zugetropft. Nach zweistündigem. Erhitzen auf<B>90-100 0</B> wird die Reaktionsmischung in<B>1000</B> cm3 2n-NaOH eingetragen und die ausgeschiedene Base in Äther aufgenommen.
Durch Auszie- hen der ätherischen Lösung mit 10 %iger Essigsäure und Zerlegen der essigsauren Lösung mit Pottasche und Äther wird die Base gereinigt und zuletzt durch Dampf- destillation von den letzten Resteri des über schüssigen aliphatischen Diamins befreit.
Man fällt ans der gut getrockneten ätherischen Lösung mit ätherischer Chlorwasserstoffsäure das Dihydroeblorid des erhaltenen 6-Chlor-9- (a-diäthylamii-lo-O'-pentyl-amino)-aeridins,. das durch Umkristallisieren aus wenig Alkohol in gelben leicht mit gelber Farbe und grüner Fluoreszenz wasserlöslichen Kristallen vom Zersetzungspunkt 234-2361 gewonnen wird.
Durch Umsetzung der wäs8erigen Lösung mit Alkalien erhält man die freie Base<B>in</B> Form eines gelben, in Äther, Benzol, Alkohol, Methylenchlorid usw. leicht löslichen Öls.
Das bisher ebenfalls unbekannte 6,9-Di- chloraeridin (schwach gelbe Kriställehen aus Benzol vom Fp. <B>167-168</B> ") wird aus 3-Chlor- diphenylamin <B>- 6 -</B> earbonsäure (aus Alkohol Prismen vom Fp. 200-201 ') durch Ring- schluss und Chlorierung des entstandenen Acridons erhalten.
To represent an aeridine derivative (The subject of the present invention is a method for the preparation of the previously unknown 6-chloro-9- (a-diethylamino-8-pentylamino) -aeridine, which is to be used as a remedy.
It is characterized in that 1 mol of a-diethylamino-O'-ainiiiopentane is allowed to act on <B> 1 </B> mol 6,9-dichloroacridine.
<I> Example: </I> 24.8 g of 6,9-dichloroacridine are melted together with <B> 125 </B> g of phenol in the surrounding water bath and <B> 17 </B> g of a- Diethylamino-8-aminopentane was added dropwise. After two hours. Heating to 90-100 0, the reaction mixture is introduced into 1000 cm 3 of 2N NaOH and the base which has separated out is taken up in ether.
By extracting the ethereal solution with 10% acetic acid and decomposing the acetic acid solution with potash and ether, the base is purified and finally freed from the last residues of the excess aliphatic diamine by steam distillation.
The dihydrochloride of the 6-chloro-9- (a-diäthylamii-lo-O'-pentyl-amino) -aeridine obtained is precipitated from the well-dried ethereal solution with ethereal hydrochloric acid. which is obtained by recrystallization from a little alcohol in yellow easily water-soluble crystals with a yellow color and green fluorescence with a decomposition point 234-2361.
By reacting the aqueous solution with alkalis, the free base is obtained in the form of a yellow oil that is easily soluble in ether, benzene, alcohol, methylene chloride, etc.
The also previously unknown 6,9-dichloroeridine (pale yellow crystals of benzene with a melting point of 167-168 ") is made from 3-chlorodiphenylamine <B> - 6 - </B> carboxylic acid (from alcohol prisms of melting point 200-201 ') obtained by ring closure and chlorination of the acridone formed.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE158148X | 1930-11-01 | ||
| CH154953T | 1931-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH158148A true CH158148A (en) | 1932-10-31 |
Family
ID=25716526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH158148D CH158148A (en) | 1930-11-01 | 1931-10-31 | Process for the preparation of an acridine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH158148A (en) |
-
1931
- 1931-10-31 CH CH158148D patent/CH158148A/en unknown
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