DE828247C - Process for the preparation of nicotinic acid amide - Google Patents
Process for the preparation of nicotinic acid amideInfo
- Publication number
- DE828247C DE828247C DEP16555D DEP0016555D DE828247C DE 828247 C DE828247 C DE 828247C DE P16555 D DEP16555 D DE P16555D DE P0016555 D DEP0016555 D DE P0016555D DE 828247 C DE828247 C DE 828247C
- Authority
- DE
- Germany
- Prior art keywords
- nicotinic acid
- acid amide
- preparation
- hydrogen peroxide
- solution
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung von Nicotinsäureamid Das Nicotinsäureamid erhält man durch Umsetzung der Nicotinsäureester mit Ammoniak, jedoch sind die Ausbeuten nach diesem Verfahren unbefriedigend. Es wurde nun gefunden, daß man das Nicotinsäureamid mit nahezu quantitativer Ausibeute erhalten kann, wenn man das Nicotinsäurenitril in schwach ätzalkalischer Lösung bei erhöhter Temperatur, zweckmäßig bei 40 bis 45°, mit einer verdünnten Lösung von Wasserstoffsuperoxyd behandelt.Process for the preparation of nicotinic acid amide The nicotinic acid amide is obtained by reacting the nicotinic acid ester with ammonia, but the yields are unsatisfactory after this process. It has now been found that nicotinic acid amide can be used can be obtained with almost quantitative yield if you use the nicotinonitrile in a weakly alkaline solution at elevated temperature, expediently at 40 to 45 °, treated with a dilute solution of hydrogen peroxide.
Es ist bereits vorgeschlagen worden, bestimmte Nitrile mit Wasserstoffsuperoxyd zu den Säureamiden umzusetzen, jedoch ist erwähnt, daß die Reaktion nicht allgemeiner Anwendung fähig ist und häufig bei Vergrößerung der Ansätze versagt. Infolgedessen war nicht zu erwarten, daß sie im Falle des Nicotinsäurenitrils mit so guter Ausbeute verläuft, zumal zu befürchten war, daß unerwünschte Oxydationsreaktionen eintreten würden. Beispiel 312 g Nicotinsäurenitril werden in 1500 ccm Wasser gelöst und 30 g Nat.riunnhydroxyd 'leinzugegeben. Zu der au-f 42° erwärmten Lösung werden unter gutem Rühren im Laufe von einer Stunde io5o ccm io°/oi,ge wäßrige Wasserstoffsuperoxydlösunig hinzugetropft. Es tritt unter Sauerstoffentwicklung Reaktion ein. Durch Kühlen sorgt man dafür, daß die Innentemperatur stets auf 42° gehalten wird. Nach Beendigung des Zutropfens rührt man noch eine Stunde bei 42° nach, stumpft das Alkali durch Zugabe der berechneten Menge Säure oder Ammoniumchlorid ab und dampft im Vakuum zur Trockne. Man erhält einen gelblich gefärbten Kristallkuchen, der -das Nicotinsäureamid in nahezu quantitativer Ausbeute neben den durch Neutralisation des Alkalis entstandenen anorganischen Salzen enthält. Durch Umkristallisation'. aus Isopropylalkohol oder Butylacetat in Gegenwart von Entfärbungskohle erhält man es in rein weißer Form vom Schmelzpunkt t22°.It has already been proposed to convert certain nitriles with hydrogen peroxide to form the acid amides, but it is mentioned that the reaction is not generally applicable and often fails when the batches are enlarged. As a result, it was not to be expected that it would proceed with such good yield in the case of nicotinonitrile, especially since it was to be feared that undesired oxidation reactions would occur. Example 312 g of nicotinic acid nitrile are dissolved in 1500 cc of water and 30 g of sodium hydroxide are added. To the solution heated to 42 °, 1050 ccm of 10% aqueous hydrogen peroxide solution is added dropwise over the course of one hour, with thorough stirring. A reaction occurs with evolution of oxygen. Cooling ensures that the internal temperature is always kept at 42 °. After the end of the dropwise addition, the mixture is stirred for a further hour at 42 °, the alkali is blunted by adding the calculated amount of acid or ammonium chloride and evaporated to dryness in vacuo. A yellowish colored crystal cake is obtained which contains the nicotinic acid amide in almost quantitative yield in addition to the inorganic salts formed by neutralization of the alkali. By recrystallization '. from isopropyl alcohol or butyl acetate in the presence of decolorizing charcoal, it is obtained in a pure white form with a melting point of t22 °.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP16555D DE828247C (en) | 1948-10-02 | 1948-10-02 | Process for the preparation of nicotinic acid amide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP16555D DE828247C (en) | 1948-10-02 | 1948-10-02 | Process for the preparation of nicotinic acid amide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE828247C true DE828247C (en) | 1953-07-02 |
Family
ID=7366099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP16555D Expired DE828247C (en) | 1948-10-02 | 1948-10-02 | Process for the preparation of nicotinic acid amide |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE828247C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1198824B (en) * | 1955-04-20 | 1965-08-19 | Distillers Co Yeast Ltd | Process for the preparation of nicotinic acid amide from 3-cyanopyridine |
| EP0045079A1 (en) * | 1980-07-30 | 1982-02-03 | Degussa Aktiengesellschaft | Method for the purification of nicotin amide I |
| US4447614A (en) * | 1980-07-30 | 1984-05-08 | Degussa Aktiengesellschaft | Process for the purification of nicotinic acid amide |
| WO1990009988A2 (en) * | 1989-03-02 | 1990-09-07 | Interox Chemicals Limited | Amide preparation |
-
1948
- 1948-10-02 DE DEP16555D patent/DE828247C/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1198824B (en) * | 1955-04-20 | 1965-08-19 | Distillers Co Yeast Ltd | Process for the preparation of nicotinic acid amide from 3-cyanopyridine |
| EP0045079A1 (en) * | 1980-07-30 | 1982-02-03 | Degussa Aktiengesellschaft | Method for the purification of nicotin amide I |
| US4447614A (en) * | 1980-07-30 | 1984-05-08 | Degussa Aktiengesellschaft | Process for the purification of nicotinic acid amide |
| US4447615A (en) * | 1980-07-30 | 1984-05-08 | Degussa Aktiengesellschaft | Process for the purification of nicotinic acid amide I |
| WO1990009988A2 (en) * | 1989-03-02 | 1990-09-07 | Interox Chemicals Limited | Amide preparation |
| WO1990009988A3 (en) * | 1989-03-02 | 1990-10-18 | Interox Chemicals Ltd | Amide preparation |
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