CH147076A - Process for the preparation of 2,6-diamino-2'-butyloxy-3.5'-azopyridine. - Google Patents
Process for the preparation of 2,6-diamino-2'-butyloxy-3.5'-azopyridine.Info
- Publication number
- CH147076A CH147076A CH147076DA CH147076A CH 147076 A CH147076 A CH 147076A CH 147076D A CH147076D A CH 147076DA CH 147076 A CH147076 A CH 147076A
- Authority
- CH
- Switzerland
- Prior art keywords
- butyloxy
- azopyridine
- preparation
- diamino
- salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- WAWDOEHEAULMGC-UHFFFAOYSA-N 3-[(6-butoxypyridin-3-yl)diazenyl]pyridine-2,6-diamine Chemical compound C1=NC(OCCCC)=CC=C1N=NC1=CC=C(N)N=C1N WAWDOEHEAULMGC-UHFFFAOYSA-N 0.000 title claims description 3
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 230000001225 therapeutic Effects 0.000 claims description 2
- DAFKCYYRSZSMAJ-UHFFFAOYSA-N 6-butoxypyridin-3-amine Chemical compound CCCCOC1=CC=C(N)C=N1 DAFKCYYRSZSMAJ-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- -1 2-butyloxy - 5 - aminopyridine chlorohydrate Chemical compound 0.000 description 2
- GEMGCBQSLUFODV-UHFFFAOYSA-N 2-butoxy-5-nitropyridine Chemical compound CCCCOC1=CC=C([N+]([O-])=O)C=N1 GEMGCBQSLUFODV-UHFFFAOYSA-N 0.000 description 1
- BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 1
- SFDLGENZIBLWCA-UHFFFAOYSA-N 6-butylpyridin-3-amine Chemical compound CCCCC1=CC=C(N)C=N1 SFDLGENZIBLWCA-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial Effects 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Description
Verfahren zur Darstellung von 2.6-Diamino-2'-uutyloay-3.5'-azopyridin. In dem Hauptpatent ist ein Verfahren zur Darstellung von 2.6-Diainino-2'-oxy-3.5'- azopyridin beschrieben, das darin besteht, dass 2-Oxy-5-aminopy @idiri dianotiert und die entstandene Diazoverbindungmit 2.6-Diamino- pyridin gekuppelt wird.
Benutzt man zur Dianotierung an Stelle des 2-Oxy-5-amino- pyridins das 2-Butyl-5-aminopyridin, und kuppelt man die entstandene Diazoverbindung mit 2.6-Diaminopyridin, so erhält man das 2.6-Diamino-2'-butyloxy-3.5'-azopyridin, das sich ebenfalls durch hervorragende bakterizide Eigenschaften auszeichnet. Das 2.6-Diamino- 2'-butyloxy-3.5'-azopyridin bildet rote Nadeln vom Schmelzpunkt 12911 C, mit Säure bildet es Salze; es dient als solches oder in Form seiner Salze therapeutischen Zwecken.
<I>Beispiel</I> 23 gr 2-Butyloxy - 5 - aminopyridinchlor- hydrat (hergestellt durch Einwirkung von Natriumbutylat auf 2-Chlor-5-nitropyridin in ätherischer Lösung und Reduktion des bei <B>1530</B> C unter 14 mm Druck übergehenden 2 - Butyloxy - 5 - nitropyridirrs mittelst Zinn- chlorür) werden dianotiert und mit 10.9 gr 2.6-Diaminopyridin gekuppelt. Die Base wird ausgefällt und aus Alkohol umkristallisiert.
Sie bildet rotbraune Nadeln vom Schmelz punkt 129 C.
Process for the preparation of 2.6-diamino-2'-uutyloay-3.5'-azopyridine. The main patent describes a process for the preparation of 2,6-diainino-2'-oxy-3.5'-azopyridine, which consists in dianotating 2-oxy-5-aminopy @idiri and coupling the resulting diazo compound with 2,6-diamino pyridine .
If 2-butyl-5-aminopyridine is used instead of 2-oxy-5-aminopyridine for dianotation and the resulting diazo compound is coupled with 2,6-diaminopyridine, then 2,6-diamino-2'-butyloxy-3.5 is obtained '-azopyridine, which is also characterized by excellent bactericidal properties. The 2,6-diamino-2'-butyloxy-3,5'-azopyridine forms red needles with a melting point of 12911 C, with acid it forms salts; it is used as such or in the form of its salts for therapeutic purposes.
<I> Example </I> 23 gr 2-butyloxy - 5 - aminopyridine chlorohydrate (produced by the action of sodium butoxide on 2-chloro-5-nitropyridine in an ethereal solution and reduction of the temperature at <B> 1530 </B> C below 2 - butyloxy - 5 - nitropyridine with a pressure of 14 mm by means of tin chlorine) are dianotized and coupled with 10.9 g of 2,6-diaminopyridine. The base is precipitated and recrystallized from alcohol.
It forms red-brown needles with a melting point of 129 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH147076T | 1929-11-08 | ||
| CH145270T | 1929-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH147076A true CH147076A (en) | 1931-05-15 |
Family
ID=25714662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH147076D CH147076A (en) | 1929-11-08 | 1929-11-08 | Process for the preparation of 2,6-diamino-2'-butyloxy-3.5'-azopyridine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH147076A (en) |
-
1929
- 1929-11-08 CH CH147076D patent/CH147076A/en unknown
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