CH127178A - Process for the preparation of 6-methoxy-8- (a-diethylamino-d-methyl-butyl) -amino-quinoline. - Google Patents
Process for the preparation of 6-methoxy-8- (a-diethylamino-d-methyl-butyl) -amino-quinoline.Info
- Publication number
- CH127178A CH127178A CH127178DA CH127178A CH 127178 A CH127178 A CH 127178A CH 127178D A CH127178D A CH 127178DA CH 127178 A CH127178 A CH 127178A
- Authority
- CH
- Switzerland
- Prior art keywords
- butyl
- amino
- methyl
- methoxy
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 claims description 3
- 229940000488 arsenic acid Drugs 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 2
- 210000004369 blood Anatomy 0.000 claims description 2
- 244000045947 parasite Species 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VUJSQJDPBROTSY-UHFFFAOYSA-N n-(2-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C(N)=C1 VUJSQJDPBROTSY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- PTECIXPBVVDNOU-UHFFFAOYSA-N molecular bromine;hydrate Chemical compound O.BrBr PTECIXPBVVDNOU-UHFFFAOYSA-N 0.000 description 1
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 1
- QGEGALJODPBPGR-UHFFFAOYSA-N n-(4-methoxy-2-nitrophenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C([N+]([O-])=O)=C1 QGEGALJODPBPGR-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von 6-llethoxy-8-(a-diätliylamino-ö-methyl-butyl)-amino- chinolin. Der Gegenstand des vorliegenden Paten tes betrifft ein Verfahren zur Darstellung von 6-1Tethoxy- 8-(a-diäthylamino-ö-methyl-butyl)- aininochinolin;
das Verfahren ist dadurch gekennzeichnet, dass man das zum Beispiel aus 2-Amino-4-methoxy-l-acetylaminobenzol durch Überführen in das N-diäthylamino-ö- methyl-butyl-2-amino-4 -m ethoxy-l-acetylami- nobenzol und Abspalten der Acetylgruppe erhältliche N-Diäthylamino-ö-niethyl-butyl-2- amino-4-methoxy-l-aminobenzol mit Glycerin, Schwefelsäure und Arsensäure erhitzt. Die neue Verbindung ist ein gelbgefärbtes 01, das unter 2 mm Druck bei 189-190' siedet.
Sie bildet ein kristallinisches, gelbrotes, in Wasser leicht lösliches Chlorhydrat und soll als Heilmittel gegen Blutparasiten Verwen dung finden.
<I>Beispiel:</I> Zur Darstellung von 6-Methoxy-8-(a-di- äthylamiiio-ö-methyl-butyl)-aminochinolin.
EMI0001.0018
wird das bekannte 2-Nitro-4-methoxy-l-ace- tylaminobenzol vom Schmelzpunkt<B>117'</B> mit Eisen und Essigsäure reduziert. Hierzu wer den 100 gr Eisenmehl mit 500 cm' Wasser und 12 cm' Essigsäure kochend angeätzt und <B>100</B> gr der Nitroverbindung in einer halben Stunde eingetragen, eine Stunde kochend ge halten und dann heiss abgesaugt.
Beim Er kalten kristallisiert das in heissem Wasser leicht lösliche 2-Amino-4-methoxy-l-acetyl- aminobenzol in Blättchen vom Schmelzpunkt 1450 aus. 180 Gewichtsteile dieser Verbin dung werden mit 303 Gewichtsteilen Brom hydrat des a-Diäthylamino-8-methylbutylbro- mids während 8-10 Stunden bei 100-110 verschmolzen. Die Schmelze wird in Wasser gelöst, alkalisch gemacht und 3-4 Stunden zur Entacetylierung im Wasserbad erhitzt.
Die sich ölig abscheidende Base, das N-Di- äthyl ami n o -49-m ethyl-b utyl-2-am in o-4-m eth ogy- 1-aminobenzol, wird in Äther aufgenommen und destilliert. Sie zeigt Kp 2 mm<B>205-2100</B> und stellt ein farbloses, zähflüssiges<B>01</B> dar.
600 gr dieses Aminobenzolderivates werden mit 425 gr Arsensäure und 1500 gr ent wässertem Glycerin auf 140-150' (Innen temperatur) unter Rühren am Rückfluss er hitzt. Innerhalb einer Stunde werden 400 cms konzentrierter Schwefelsäure eingetragen und zur Beendigung der Reaktion die Temperatur noch 4 Stunden auf 140-150 gehalten. Durch Austragen auf Eis, Alkalischmachen und Ausäthern wird die sich ölig abschei dende Chinolinbase abgetrennt und durch Destillation gereinigt.
Sie zeigt den Siede punkt 189-190 bei 2 mm Druck.
Process for the preparation of 6-llethoxy-8- (a-diätliylamino-ö-methyl-butyl) -amino-quinoline. The subject of the present patent relates to a process for the preparation of 6-1-thoxy-8- (a-diethylamino-ö-methyl-butyl) - ainochinolin;
The process is characterized in that the 2-amino-4-methoxy-1-acetylaminobenzene, for example, is converted into N-diethylamino-ö-methyl-butyl-2-amino-4-methoxy-1-acetylami- Nobenzene and cleavage of the acetyl group obtainable N-diethylamino-ö-niethyl-butyl-2-amino-4-methoxy-1-aminobenzene heated with glycerol, sulfuric acid and arsenic acid. The new compound is a yellow-colored oil that boils at 189-190 'under 2 mm pressure.
It forms a crystalline, yellow-red chlorine hydrate that is easily soluble in water and is said to be used as a remedy for blood parasites.
<I> Example: </I> For the preparation of 6-methoxy-8- (a-di- äthylamiiio-ö-methyl-butyl) -aminoquinoline.
EMI0001.0018
the known 2-nitro-4-methoxy-1-acetylaminobenzene with a melting point of 117 'is reduced with iron and acetic acid. For this purpose, the 100 g iron flour is etched with 500 cm 'water and 12 cm' acetic acid and <B> 100 </B> g of the nitro compound is added in half an hour, kept boiling for one hour and then vacuumed hot.
When it is cold, 2-amino-4-methoxy-1-acetylaminobenzene, which is readily soluble in hot water, crystallizes out in flakes with a melting point of 1450. 180 parts by weight of this compound are fused with 303 parts by weight of bromine hydrate of α-diethylamino-8-methylbutyl bromide for 8-10 hours at 100-110. The melt is dissolved in water, made alkaline and heated in a water bath for 3-4 hours for deacetylation.
The base which separates out oily, the N-diethyl amin o -49-m ethyl-butyl-2-am in o-4-methoxy-1-aminobenzene, is taken up in ether and distilled. It shows Kp 2 mm <B> 205-2100 </B> and represents a colorless, viscous <B> 01 </B>.
600 grams of this aminobenzene derivative are refluxed with 425 grams of arsenic acid and 1500 grams of drained glycerol to 140-150 '(internal temperature) while stirring. 400 cms of concentrated sulfuric acid are introduced over the course of one hour and the temperature is maintained at 140-150 for a further 4 hours to complete the reaction. The quinoline base which separates out oily is separated off by discharging onto ice, rendering alkaline and etherifying and purified by distillation.
It shows the boiling point 189-190 at 2 mm pressure.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE127178X | 1924-09-11 | ||
| CH125832T | 1925-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH127178A true CH127178A (en) | 1928-08-16 |
Family
ID=25710564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH127178D CH127178A (en) | 1924-09-11 | 1925-08-08 | Process for the preparation of 6-methoxy-8- (a-diethylamino-d-methyl-butyl) -amino-quinoline. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH127178A (en) |
-
1925
- 1925-08-08 CH CH127178D patent/CH127178A/en unknown
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