CH96608A - Process for the preparation of an acridine derivative. - Google Patents
Process for the preparation of an acridine derivative.Info
- Publication number
- CH96608A CH96608A CH96608DA CH96608A CH 96608 A CH96608 A CH 96608A CH 96608D A CH96608D A CH 96608DA CH 96608 A CH96608 A CH 96608A
- Authority
- CH
- Switzerland
- Prior art keywords
- acridine
- preparation
- methoxy
- acridine derivative
- diamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 title 1
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- WKVOIVFMECKPLR-UHFFFAOYSA-N 1-methoxyacridine-2,3-diamine Chemical compound NC=1C(=C(C2=CC3=CC=CC=C3N=C2C=1)OC)N WKVOIVFMECKPLR-UHFFFAOYSA-N 0.000 description 1
- -1 B. phenylhydrazine Chemical compound 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
Description
Verfahren zur Darstellung eines Aeridinderivates. Es wurde gefunden, dass man in dem Ver fahren des Zusatzpatentes Nr. 94625 an Stelle von 3 # 9 # 7-Niti-o-amino-methoxy-aci-idin, aus welchem man durch Behandlung mit Reduk tionsmitteln zu dem 3 # 9 # 7-Diamino-methoxy- acridin gelangt,
auch ein aus dein 3 # 9 # 7- Nitro-chlor-ixietlioxy-aeridiii durch Umsetzung mit einem Hydrazin, z. B. Phenylhydrazin, erhältliches 3 # 9 # 7-Niti#o-hydrazino-inethoxy- acridin verwenden kann.
Das 3 # 7 # 9-Nitro- methoxy-phenylhydrazirio-acridin ist eine rote Verbindung, unlöslich in Wasser, löslich in Alkohol, ihr Schmelzpunkt liegt höher als 300 ; als Chlorhydrat ist sie in Wasser sehr schwer löslich.
<I>Beispiel:</I> 27 Teile 3.7.9-Nitro-methoxy-phenyl- liydrazirio-acridin-chlorhydrat werden mit 300 Teilen Wasser, 100 Teilen Alkohol, 5 Teilen Salmiak und 44 Teilen Zinkstaub einige Stunden zum Sieden erhitzt, sodann wird der Alkohol abdestilliert, die wässerige Lösung abfiltriert und aus ihr durch Salzsäure das Diamino-methoxy-acridin als salzsaures Salz gefällt; es bildet gelbe Nadeln, die aus ihr abgeschiedene Base schmilzt bei 240-2420.
Process for the preparation of an aeridine derivative. It was found that in the process of additional patent no. 94625 instead of 3 # 9 # 7-Niti-o-amino-methoxy-aci-idin, from which one can by treatment with reducing agents to the 3 # 9 # 7-diamino-methoxy-acridine arrives,
also one from your 3 # 9 # 7-nitro-chloro-ixietlioxy-aeridiii by reaction with a hydrazine, e.g. B. phenylhydrazine, available 3 # 9 # 7-Niti # o-hydrazino-inethoxy-acridine can use.
The 3 # 7 # 9-nitro-methoxy-phenylhydrazirio-acridine is a red compound, insoluble in water, soluble in alcohol, its melting point is higher than 300; as a chlorine hydrate it is very sparingly soluble in water.
<I> Example: </I> 27 parts of 3.7.9-nitro-methoxy-phenyl-liydrazirio-acridine chlorohydrate are heated to the boil for a few hours with 300 parts of water, 100 parts of alcohol, 5 parts of ammonia and 44 parts of zinc dust the alcohol is distilled off, the aqueous solution is filtered off and the diamino-methoxy-acridine is precipitated from it as a hydrochloric acid salt using hydrochloric acid; it forms yellow needles, the base deposited from it melts at 240-2420.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE96608X | 1920-10-28 | ||
| CH93439T | 1921-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH96608A true CH96608A (en) | 1922-11-01 |
Family
ID=25704670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH96608D CH96608A (en) | 1920-10-28 | 1921-08-11 | Process for the preparation of an acridine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH96608A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4544659A (en) * | 1982-11-26 | 1985-10-01 | Hoffman-La Roche Inc. | Schistosomicidal acridanone hydrazones |
| US4711889A (en) * | 1983-11-15 | 1987-12-08 | Hoffman-La Roche Inc. | Schistosomicidal acridanone hydrazones |
-
1921
- 1921-08-11 CH CH96608D patent/CH96608A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4544659A (en) * | 1982-11-26 | 1985-10-01 | Hoffman-La Roche Inc. | Schistosomicidal acridanone hydrazones |
| US4711889A (en) * | 1983-11-15 | 1987-12-08 | Hoffman-La Roche Inc. | Schistosomicidal acridanone hydrazones |
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