DE476458C - Process for the preparation of 2-aminopyridine - Google Patents
Process for the preparation of 2-aminopyridineInfo
- Publication number
- DE476458C DE476458C DED49457D DED0049457D DE476458C DE 476458 C DE476458 C DE 476458C DE D49457 D DED49457 D DE D49457D DE D0049457 D DED0049457 D DE D0049457D DE 476458 C DE476458 C DE 476458C
- Authority
- DE
- Germany
- Prior art keywords
- aminopyridine
- pyridine
- preparation
- sodium amide
- temperatures
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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
- C07D213/73—Unsubstituted amino or imino radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Darstellung von 2-Aminopyridin Durch die Arbeit von S a c h s (Berichte 39 f igo6] , Seite 3oo6 ff.) ist die Einführung der Aminogruppe in den Kern carbozyklischer Verbindungen durch Behandlung derselben mit Natriumamid bekannt geworden. Später hat dann Tschitschibabin gezeigt, daß dieselbe Reaktion auch in Anwendung auf heterozyklische Verbindungen durchgeführt werden kann (vgl. Chemisches Zentralblatt igi5, I, Seite io64). Die Darstellung von 2-Aminopyridin wird nach Tschitschib a b i n derart vorgenommen, daß gleiche Moleküle Pyridin und Natriumamid auf Temperaturen von 120 bis 15o° erhitzt werden. Nach der Patentschrift 362 446 erhält man bei Einhaltung dieser Vorschrift nur ein sehr unreines und zudem schwer zu reinigendes Produkt. Zwecks Behebung dieses Nachteils hat der Inhaber des Patentes 362 446 vorgeschlagen, auf i Mol. Pyridin 2 Mol. Natriumamid anzuwenden. Auch bei diesem Verfahren wurde bei Temperaturen oberhalb 7201 (i2o bis i30°) gearbeitet.Process for the preparation of 2-aminopyridine Through the work of S achs (Reports 39 f igo6], page 3oo6 ff.), The introduction of the amino group into the core of carbocyclic compounds by treating them with sodium amide has become known. Chichibabin later showed that the same reaction can also be carried out when applied to heterocyclic compounds (cf. Chemisches Zentralblatt igi5, I, page 1064). According to Tschitschibabin, 2-aminopyridine is prepared in such a way that the same molecules of pyridine and sodium amide are heated to temperatures of 120 to 150 °. According to patent specification 362 446, if this rule is adhered to, only a very impure and, moreover, difficult to clean product is obtained. In order to remedy this disadvantage, the proprietor of patent 362,446 has proposed that 2 moles of sodium amide be applied to 1 mole of pyridine. This process, too, was carried out at temperatures above 7201 (i2o to i30 °).
Es wurde nun gefunden, daß man auch unter Anwendung molekularer Mengen von Pvridin und Natriumamid ein Produkt von ausgezeichneten Eigenschaften erhalten, also auf den bei den bekannten Verfahren verwendeten großen Aufwand an Natriumamid verzichten kann, wenn bei Temperaturen gearbeitet wird, welche unterhalb des bei 116 liegenden Siedepunktes des Pyridins gehalten werden. - Beispiel In einem mit Heizvorrichtung, Rührwerk und Rückflußkühler versehenen Gefäß wird ein Gemisch gleicher Moleküle mit Pyridin und grob gemahlenem Natriumamid verdünnt mit einem indifferenten Mittel; z. B. Toluol, angewärmt. Hierbei ist die in der Zeiteinheit entwickelte Gasmenge ein Maß für die Reaktionsgeschwindigkeit. Bis etwa 65° C findet nur schwache Gasentwicklung statt; von da an bis etwa 97° C steigert sich dann die Gasentwicklung, um dann wieder bei nunmehr nahezu gleichbleibender Temperatur wieder rasch abzunehmen. Der Höhepunkt der Reaktion wird bei der obigen Arbeitsweise mithin bei etwa 97° erreicht. Das erhaltene 2-Aminopyridin besitzt einen ausgezeichneten Reinheitsgrad. Die Ausbeute beträgt im allgemeinen etwa 8o °/a. Durch Umkristallisieren erhält man die Verbindung in Form weißer Blätter vom Schmelzpunkt 591.It has now been found that one can also use molecular quantities obtained from pvridine and sodium amide a product with excellent properties, thus on the great expense of sodium amide used in the known processes can do without when working at temperatures which are below the at 116 lying boiling point of pyridine can be maintained. - Example In one with The vessel provided with the heating device, stirrer and reflux condenser becomes a mixture of the same Molecules with pyridine and coarsely ground sodium amide diluted with an indifferent one Middle; z. B. toluene, warmed. Here is the one developed in the unit of time Amount of gas is a measure of the rate of reaction. Up to about 65 ° C takes place only weak Gas evolution takes place; from then on up to about 97 ° C the gas development increases, in order to then quickly decrease again at a temperature that is now almost the same. With the above procedure, the peak of the reaction is therefore at about 97 ° achieved. The 2-aminopyridine obtained has an excellent degree of purity. The yield is generally about 80% / a. Obtained by recrystallization the compound is in the form of white leaves with a melting point of 591.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DED49457D DE476458C (en) | 1925-12-17 | 1925-12-17 | Process for the preparation of 2-aminopyridine |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DED49457D DE476458C (en) | 1925-12-17 | 1925-12-17 | Process for the preparation of 2-aminopyridine |
Publications (1)
Publication Number | Publication Date |
---|---|
DE476458C true DE476458C (en) | 1929-05-18 |
Family
ID=7051910
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DED49457D Expired DE476458C (en) | 1925-12-17 | 1925-12-17 | Process for the preparation of 2-aminopyridine |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE476458C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2807619A (en) * | 1956-07-23 | 1957-09-24 | Reilly Tar & Chem Corp | 2-aminoalkanolpyridines |
-
1925
- 1925-12-17 DE DED49457D patent/DE476458C/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2807619A (en) * | 1956-07-23 | 1957-09-24 | Reilly Tar & Chem Corp | 2-aminoalkanolpyridines |
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