DEF0010223MA - - Google Patents
Info
- Publication number
- DEF0010223MA DEF0010223MA DEF0010223MA DE F0010223M A DEF0010223M A DE F0010223MA DE F0010223M A DEF0010223M A DE F0010223MA
- Authority
- DE
- Germany
- Prior art keywords
- cinnamaldehyde
- acid hydrazide
- isonicotinic acid
- hydrate
- parts
- 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.)
- Active
Links
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 7
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims description 6
- 229940117916 cinnamic aldehyde Drugs 0.000 claims description 6
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001241 acetals Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002373 hemiacetals Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000007857 hydrazones Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- -1 benzal compounds Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
Tag· der Anmeldung: 31. Juli 1951 Bekanntgeniacht am 12. April 1956Date of registration: July 31, 1951 Announced on April 12, 1956
DEUTSCHES PATENTAMTGERMAN PATENT OFFICE
Das Isonicotinsäurehydrazid sowie die drei bekannten Benzalverbindungen desselben besitzen, *' wie gefunden wurde, eine gewisse Wirksamkeit gegenüber säurefesten Bakterien, wie Mycobacte-S riuni tuberculosis.The isonicotinic acid hydrazide and the three known benzal compounds of the same have, * 'has been found to have some effectiveness against acid-fast bacteria such as Mycobacte-S riuni tuberculosis.
Es wurde nun die überraschende Beobachtung gemacht, daß man zu einer Verbindung mit erhöhter Wirksamkeit gegenüber säurefesten Bakterien gelangt, wenn man Isonicotinsäurehydrazid ίο mit Zimtaldehyd umsetzt.The surprising observation has now been made that a connection with increased Effectiveness against acid-fast bacteria comes from taking isonicotinic hydrazide ίο reacts with cinnamaldehyde.
Die Umsetzung des Isonicotinsäurehydrazids mit Zimtaldehyd kann so vorgenommen werden, daß man die Reaktionsteilnehmer als solche miteinander vereinigt, wobei man im Schmelzfluß oder in Lösung arbeiten kann. Man kann jedoch auch so verfahren, daß man das Isonicotinsäurehydrazid in Form seiner Salze mit sauer reagierenden Verbindungen, z. B. der Hydrochloride, zur Umsetzung bringt. Dabei ist es nicht immer erforderlich, von Zimtaldehyd als solchem auszugehen. Vielmehr ist es gelegentlich vorteilhaft, ihn in Form seines Hydrates oder eines Halbacetals, Acetals oder Hydratesters zu verwenden.The reaction of isonicotinic acid hydrazide with cinnamaldehyde can be carried out in such a way that that the reactants are combined with one another as such, being in the melt flow or can work in solution. However, one can also proceed in such a way that the isonicotinic acid hydrazide is used in the form of its salts with acidic compounds, e.g. B. the hydrochloride, for Implementation brings. It is not always necessary to start with cinnamaldehyde as such. Rather, it is occasionally advantageous to use it in the form of its hydrate or a hemiacetal, acetal or hydrate esters to be used.
Die Reaktionen verlaufen im allgemeinen bei normaler oder mäßig erhöhter Temperatur; die Anwendung von Temperaturen über 100 oder unter o° ist in einzelnen Fällen zweckdienlich.The reactions generally take place at normal or moderately elevated temperatures; the Use of temperatures above 100 or below 0 ° is appropriate in individual cases.
Bei Verbindungen, die durch Luftsauerstoff oder Oxydationsmittel verändert werden, arbeitet man am besten in Gegenwart solcher Mittel, die denYou work with compounds that are changed by atmospheric oxygen or oxidizing agents best in the presence of such means that the
509 704/380509 704/380
F 10223 IVb/12 pF 10223 IVb / 12 p
Sauerstoff verdrängen oder die reduzierend wirken, oder unter Luftabschluß. Im allgemeinen verlaufen die Reaktionen ohne katalytisch wirkende Zugaben, jedoch kann der Zusatz von sauer reagierenden Verbindungen den Ablauf der Reaktion erleichtern oder beschleunigen.Displace oxygen or have a reducing effect, or in the absence of air. Generally run the reactions without catalytically active additions, however, the addition of acidic reacting Compounds facilitate or accelerate the course of the reaction.
Im Beispiel verhalten sich die Volumteile zu den Gewichtsteilen wie 1 zu kg.In the example, the parts by volume relate to parts by weight like 1 to kg.
69 Gewichtsteile Isonicotinsäurehydrazid werden in 2000 Volumteilen Alkohol gelöst und in der Siedehitze mit 60 Gewichtsteilen Zimtaldehyd versetzt. Der alsbald ausfallende Niederschlag wird abgesaugt und schmilzt bei 2020. Die Ausbeute beträgt 83%. Aus den Mutterlaugen lassen sich weitere Anteile durch Fällen mit Wasser gewinnen, die durch Umkristallisieren aus Methanol gereinigt werden können.69 parts by weight of isonicotinic acid hydrazide are dissolved in 2000 parts by volume of alcohol and 60 parts by weight of cinnamaldehyde are added at the boiling point. The precipitate which soon separates out is suctioned off and melts at 202 ° . The yield is 83%. Further fractions can be obtained from the mother liquors by precipitation with water, which can be purified by recrystallization from methanol.
Claims (1)
Zeitschrift für Naturforschung, Bd. 7b, S. 466, (1952).Referred publications:
Zeitschrift für Naturforschung, Vol. 7b, p. 466, (1952).
Family
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