CH154173A - Process for the preparation of 5,6-dimethoxy-8-aminoquinoline. - Google Patents
Process for the preparation of 5,6-dimethoxy-8-aminoquinoline.Info
- Publication number
- CH154173A CH154173A CH154173DA CH154173A CH 154173 A CH154173 A CH 154173A CH 154173D A CH154173D A CH 154173DA CH 154173 A CH154173 A CH 154173A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethoxy
- aminoquinoline
- weight
- parts
- preparation
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 5.6-Dimethoxy-8-aminochinolin. Gegenstand vorliegender Erfindung ist ein Verfahren zur Darstellung des als Zwi schenprodukt für die Herstellung von Farb stoffen und Arzneimitteln verwendbaren 5 .
6 - Dimethoxy-8-aminochinolins, dadurch gekennzeichnet, dass man 5 - Halogen - 6 - nietlioxy-8-nitrochinolin mit einem Meta11- methylat, insbesondere Alkalimethylat be handelt und das gebildete 5.6-Dimethoxy- 8-nitroehinolin reduziert.
<I>Beispiel:</I> 5.6-Dimetlboxy-8-nitrochinolin: 28,3 Gewichtsteile 5 -Brom - 6 - methoxy - 8 -nitro- chinolin (F. 20,5 bis 206 ) werden: in einer Lösung von 2,3 Gewichtsteilen Natrium in <B>1600</B> Gewichtsteilen Methylalkohol 6 Stun den bei<B>130</B> bis 140' unter Druck erhitzt.
Nach dem Erkalten wird das in Form langer Nadeln ausgeschiedene 5 . 6 - Dimethoxy - 8 - nitrochinolin abgesaugt. Es, zeigt den Schmelzpunkt 126 bis 128 . Die Ausbeute beträgt etwa. 85 %.
Die gleiche Verbindung erhält man mit ähnlicher Ausbeute, wenn man 238 Gewichts teile 5-Chlor-6-methoxy-8-nitroehinolin (F. 202 bis! 203 ) mit einer Lösung von 1 Mol Natriummethyla.t in 4000 Gewichtsteilen Methylalkohol einige Tage zum Sieden er hitzt und das Reaktionsprodukt nach dem Abdampfen des überschüssigen Methylalho- hols wie oben abscheidet.
<I>b)</I> 5.6-Dimethoxy-8-aminochi-nolin. <I>30</I> Gewichtsteile 5 . 6 - Dimethoxy-8-nitrocliino- lin werden langsam in eine siedende Mi schung von 300 Gewichtsteilen Eisenmehl. 500 Gewichtsteilen Wasser und 2 Gewichts teilen Eisessig innerhalb drei Stunden ein getragen.
Nach Beendigung der Umsetzung wird mit galiumkarbonat alkalisch gemacht und die Reaktionsmischung wiederholt aus- geäthert. Aus dem Äther kristallisiert beim Tindampfen das 5.6-Dimethoxy-8-amino- chinolin in hellgelben Kristallen vom Schmelzpunkt 148' aus. Die Ausbeute be trägt 80 bis 90 %.
Die Reduktion lässt sich auch mittelst Zinnchloriir in Eisessiglösung durchführen.
Process for the preparation of 5,6-dimethoxy-8-aminoquinoline. The present invention relates to a process for the preparation of the 5 which can be used as an intermediate product for the production of dyes and drugs.
6 - dimethoxy-8-aminoquinoline, characterized in that 5 - halogen - 6 - nietlioxy-8-nitroquinoline is treated with a meta11-methylate, in particular alkali metal methylate, and the 5,6-dimethoxy-8-nitroehinoline formed is reduced.
<I> Example: </I> 5.6-Dimetlboxy-8-nitroquinoline: 28.3 parts by weight of 5-bromo-6-methoxy-8-nitro-quinoline (F. 20.5 to 206) are: in a solution of 2 , 3 parts by weight of sodium in <B> 1600 </B> parts by weight of methyl alcohol for 6 hours at <B> 130 </B> to 140 'heated under pressure.
After cooling down, the 5. 6 - dimethoxy - 8 - nitroquinoline sucked off. It shows a melting point of 126 to 128. The yield is about. 85%.
The same compound is obtained with a similar yield if you boil 238 parts by weight of 5-chloro-6-methoxy-8-nitroehinoline (F. 202 to! 203) with a solution of 1 mol of sodium methyla.t in 4000 parts by weight of methyl alcohol for a few days it heats and, after the excess methyl alcohol has been evaporated off, the reaction product is deposited as above.
<I> b) </I> 5,6-dimethoxy-8-aminochinoline. <I> 30 </I> parts by weight 5. 6 - Dimethoxy-8-nitrocliino- lin are slowly mixed into a boiling mixture of 300 parts by weight of iron flour. 500 parts by weight of water and 2 parts by weight of glacial acetic acid are worn within three hours.
After the reaction has ended, it is made alkaline with galium carbonate and the reaction mixture is repeatedly extracted with ether. When evaporating tin, the 5,6-dimethoxy-8-aminoquinoline crystallizes out of the ether in light yellow crystals with a melting point of 148 '. The yield be 80 to 90%.
The reduction can also be carried out by means of tin chloride in a glacial acetic acid solution.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE154173X | 1930-02-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH154173A true CH154173A (en) | 1932-04-30 |
Family
ID=5676174
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH154173D CH154173A (en) | 1930-02-17 | 1931-02-10 | Process for the preparation of 5,6-dimethoxy-8-aminoquinoline. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH154173A (en) |
-
1931
- 1931-02-10 CH CH154173D patent/CH154173A/en unknown
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CH154173A (en) | Process for the preparation of 5,6-dimethoxy-8-aminoquinoline. | |
DE531083C (en) | Process for the preparation of 5,6-dialkoxy-8-aminoquinolines | |
AT135351B (en) | Process for the preparation of aliphatic amino alcohols. | |
DE860637C (en) | Process for the preparation of sulfur-containing cyclic organic compounds | |
DE536997C (en) | Process for the preparation of 1-methyl-4-chloro-3-oxybenzene-2-carboxylic acid | |
DE582715C (en) | Process for the preparation of 4-butylaminobenzoic acid ª ‰ -dimethylaminoaethyl ester | |
CH189749A (en) | Method for the preparation of 17-methyl-dihydrofollicle hormone. | |
CH157829A (en) | Process for the preparation of 5-methoxy-6-ethoxy-8-aminoquinoline. | |
DE512233C (en) | Process for the preparation of 1-aminocarbazole and its derivatives | |
CH217133A (en) | Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. | |
CH168923A (en) | Process for the preparation of 2-ethylaminobenzene-1-carboxylic acid-4-sulfonic acid. | |
CH160940A (en) | Process for the preparation of a 4-oxypyridine derivative. | |
CH179654A (en) | Process for the preparation of a new quaternary salt. | |
CH162654A (en) | Process for the production of an X-ray contrast medium. | |
CH117493A (en) | Process for the preparation of p-N-B-methoxyethylaminobenzoic acid-B-piperidinoethyl ester. | |
CH174886A (en) | Process for the preparation of an oxycarboxylic acid. | |
CH212595A (en) | Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position. | |
CH139430A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH191238A (en) | Process for the preparation of 3-oxycarbazole-2-carboxylic acid. | |
CH154999A (en) | Process for the preparation of a dichlorobenzene-o-oxy-carboxylic acid. | |
CH221827A (en) | Process for the production of a new condensation product. | |
CH143279A (en) | Process for the preparation of a 6-arylamino-2-naphthol-3-carboxylic acid. | |
CH199958A (en) | Process for the preparation of a 2-oxynaphthalene-4-sulfonic acid. | |
CH123734A (en) | Procedure for displaying the 1st 8-oxynaphthoic acid. | |
CH161979A (en) | Process for the preparation of 4-butylaminobenzoic acid-B-dimethylaminoethyl ester. |