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
- 238000000034 method Methods 0.000 title claims description 5
- RDFZQTDLGKFDNB-UHFFFAOYSA-N 5,6-dimethoxyquinolin-8-amine Chemical compound N1=CC=CC2=C(OC)C(OC)=CC(N)=C21 RDFZQTDLGKFDNB-UHFFFAOYSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical group 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- SDMIYMJTQNOZRV-UHFFFAOYSA-N 5-bromo-6-methoxy-8-nitroquinoline Chemical compound N1=CC=CC2=C(Br)C(OC)=CC([N+]([O-])=O)=C21 SDMIYMJTQNOZRV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
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