CH305891A - Process for the preparation of isonicotinic acid hydrazide. - Google Patents
Process for the preparation of isonicotinic acid hydrazide.Info
- Publication number
- CH305891A CH305891A CH305891DA CH305891A CH 305891 A CH305891 A CH 305891A CH 305891D A CH305891D A CH 305891DA CH 305891 A CH305891 A CH 305891A
- Authority
- CH
- Switzerland
- Prior art keywords
- isonicotinic acid
- hydrazine
- acid hydrazide
- preparation
- distilled
- Prior art date
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
- C07D213/86—Hydrazides; Thio or imino analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Isonicotinsäurehydrazid. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von Iso- nicotinsäurehydrazid.
Bekannt ist die Herstellung von Isonico- tinsäurehydrazid durch Umsatz von Isonieo- tinsäureester oder Isonicotinsäurechlor id mit Hydrazin.
Das Verfahren gemäss der Erfindung ist dadurch gekennzeichnet, dass man Isonicotin- säure mit Hydrazin in der Hitze behandelt und das beider Reaktion auftretende Wasser erbdestilliert. Das Hydrazin kann z. B. auch in Form von Hydrazinhydrat oder einer wäs serigen Hydrazinlösung eingesetzt werden.
Die Wärmezufuhr erfolgt zweckmässig durch allmähliche Temperatursteigerung bis i ui 220 C. Zweckmässig wird Hydrazin in einem Überschuss von 5-25 Mol.1/o verwendet. Das bereits bekannte Isonicotinsäurehydra- zid soll als Arzneimittel und als Zwischenpro dukt zur Herstellung von Arzneimitteln Ver wendung finden.
Beispiel: 61,5 g Isonicotinsäure werden mit 48 g 65o/oigem Hydrazinhydrat versetzt. Das Ge misch, wird in einem Destillierkolben im Ölbad erhitzt. Die Temperatur des Ölbades wird innerhalb 5 Minuten auf 190 und innerhalb weiteren 30 Minuten auf 220 gesteigert. Dann wird weitere 15 Minuten auf dieser Tempera tur gehalten, bis die theoretische Menge Was ser erbdestilliert ist. Im Kolben verbleibt eine ,Schmelze, die beim Abkühlen bei 135-1400 erstarrt.
Das so erhaltene Rohprodukt ist gelb ge färbt und wird nach bekannter Methode gerei nigt, indem die erstarrte Schmelze pulverisiert und aus 200 ems siedendem Äthanol unter Zu satz von 2 g Aktivkohle umkristallisiert wird. Es wurden 54 g Isonicotinsäurehydrazid vom Schmelzpunkt 170-171 erhalten.
Nach Einengen der alkoholischen Mutter lauge und nochmaligem Umkristallisieren des Rückstandes aus Äthanol wurde eine weitere Fraktion von 5 g vom Schmelzpunkt 169-170 erhalten.
Totalausbeute 59 g entsprechend 86 % der Theorie, bezogen auf Isonicotinsäure.
Aus den letzten Mutterlaugen kann durch mehrstündiges Erhitzen mit Salzsäure und anschliessendes Abstiunpfen bis PH = 3,3 noch etwas Isonicotinsäure zurückgewonnen wer den.
Ein Teil des Überschusses an Hydrazin geht beim Abdestillieren des Wassers mit über und kann durch Zufügen von verdünnter Schwefelsäure als schwerlösliches Hydrazin- sulfat zurückgewonnen werden.
Process for the preparation of isonicotinic acid hydrazide. The present invention relates to a process for the preparation of isonicotinic acid hydrazide.
The production of isonicotinic acid hydrazide by reacting isonicotinic acid ester or isonicotinic acid chloride with hydrazine is known.
The process according to the invention is characterized in that isonicotinic acid is treated with hydrazine in the heat and the water occurring in the reaction is earth-distilled. The hydrazine can e.g. B. can also be used in the form of hydrazine hydrate or a wäs serigen hydrazine solution.
The heat is expediently supplied by gradually increasing the temperature up to i ui 220 C. It is expedient to use hydrazine in an excess of 5-25 mol / o. The already known isonicotinic acid hydrazide is to be used as a drug and as an intermediate product for the manufacture of drugs.
Example: 61.5 g of isonicotinic acid are mixed with 48 g of 65% hydrazine hydrate. The mixture is heated in a still in an oil bath. The temperature of the oil bath is increased to 190 within 5 minutes and to 220 within a further 30 minutes. It is then held at this temperature for a further 15 minutes until the theoretical amount of water has been earth-distilled. A melt remains in the flask, which solidifies at 135-1400 on cooling.
The crude product thus obtained is yellow in color and is cleaned by a known method by pulverizing the solidified melt and recrystallizing it from 200 ems of boiling ethanol with the addition of 2 g of activated charcoal. 54 g of isonicotinic acid hydrazide with a melting point of 170-171 were obtained.
After concentrating the alcoholic mother liquor and recrystallizing the residue again from ethanol, a further fraction of 5 g with a melting point of 169-170 was obtained.
Total yield 59 g, corresponding to 86% of theory, based on isonicotinic acid.
Some isonicotinic acid can be recovered from the last mother liquors by heating them with hydrochloric acid for several hours and then tapping them off until pH = 3.3.
A part of the excess of hydrazine passes over when the water is distilled off and can be recovered as sparingly soluble hydrazine sulfate by adding dilute sulfuric acid.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH305891T | 1952-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH305891A true CH305891A (en) | 1955-03-15 |
Family
ID=4492605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH305891D CH305891A (en) | 1952-06-09 | 1952-06-09 | Process for the preparation of isonicotinic acid hydrazide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH305891A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891067A (en) * | 1957-02-08 | 1959-06-16 | Albert David Ltd | Preparation of isonicotinic acid hydrazide |
| DE1116667B (en) * | 1956-07-03 | 1961-11-09 | Basf Ag | Process for the preparation of isonicotinic acid hydrazide |
| DE1160438B (en) * | 1955-06-29 | 1964-01-02 | Distillers Co Yeast Ltd | Process for the preparation of isonicotinic acid hydrazide |
-
1952
- 1952-06-09 CH CH305891D patent/CH305891A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1160438B (en) * | 1955-06-29 | 1964-01-02 | Distillers Co Yeast Ltd | Process for the preparation of isonicotinic acid hydrazide |
| DE1116667B (en) * | 1956-07-03 | 1961-11-09 | Basf Ag | Process for the preparation of isonicotinic acid hydrazide |
| US2891067A (en) * | 1957-02-08 | 1959-06-16 | Albert David Ltd | Preparation of isonicotinic acid hydrazide |
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