CH132907A - Process for the preparation of a halogenated 2-pyridine. - Google Patents
Process for the preparation of a halogenated 2-pyridine.Info
- Publication number
- CH132907A CH132907A CH132907DA CH132907A CH 132907 A CH132907 A CH 132907A CH 132907D A CH132907D A CH 132907DA CH 132907 A CH132907 A CH 132907A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxy
- diiodopyridine
- preparation
- halogenated
- pyridine
- Prior art date
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 5
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 3
- 229960000583 Acetic Acid Drugs 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 150000003388 sodium compounds Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000003930 2-aminopyridines Chemical class 0.000 description 1
- XDELKSRGBLWMBA-UHFFFAOYSA-N 3-iodopyridine Chemical compound IC1=CC=CN=C1 XDELKSRGBLWMBA-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Verfahren zur Darstellung eines halogenierten 2-Pyridins. Bisher ist zur Gewinnung von haloge- niertem 2-Pyridon nur der Weg beschritten worden, dass man das halogenierte 2-Amino- pyridin diazatierte und durch Erwärmen mit Wasser die Diazogruppe gegen Hydroxyl austauscht.
Es wurde gefunden, dass man auch über das 2-Pyridon durch direkte Ha- logenierung gehen kann, wobei je nach den Bedingungen mono- oder dihalogenierte Verbindungen entstehen. Beim Behandeln von 2-Pyridon mit Chlorjod in saurer Lö sung erhält man das 2-Oxy-3.5-dijod- pyridin.
<I>Beispiel:</I> 20 gr 2-Pyridon werden in 25 cm' ver dünnter Salzsäure gelöst und mit 35 gr Jodmonochlorid in verdünnter Salzsäure ver setzt. Nach mehrstündigem Stehen bei ge wöhnlicher Temperatur scheidet sich das 2- Oxy-3. 5-jodpyridin in reiner Form ab.
Das 2-Oxy-3. 5-dijodpyridin bildet gelb liche Kristalle; es lässt sich aus einem Alkohol-Pyridingemisch oder aus Eisessig umkristallisieren. Es schmilzt bei 255 , bei 265 C zersetzt es sich. In heisser Natron lauge ist es löslich; beim Erkalten kristal lisiert die Natriumverbindung aus. Das 2- Oxy-3. 5-dijodpyridin soll als Zwischenpro- dukt für die Herstellung pharmazeutischer Präparate verwendet werden.
Process for the preparation of a halogenated 2-pyridine. So far, the only way to obtain halogenated 2-pyridone has been to diazate the halogenated 2-aminopyridine and exchange the diazo group for hydroxyl by heating with water.
It has been found that it is also possible to proceed via the 2-pyridone by direct halogenation, with mono- or dihalogenated compounds being formed depending on the conditions. When 2-pyridone is treated with chloroiodine in acidic solution, 2-oxy-3,5-diiodopyridine is obtained.
<I> Example: </I> 20 g 2-pyridone are dissolved in 25 cm diluted hydrochloric acid and mixed with 35 g iodine monochloride in dilute hydrochloric acid. After standing for several hours at normal temperature, the 2-Oxy-3 separates. 5-iodopyridine in its pure form.
The 2-oxy-3. 5-diiodopyridine forms yellowish crystals; it can be recrystallized from an alcohol-pyridine mixture or from glacial acetic acid. It melts at 255, at 265 C it decomposes. It is soluble in hot sodium hydroxide solution; the sodium compound crystallizes out on cooling. The 2-oxy-3. 5-diiodopyridine is intended to be used as an intermediate product for the manufacture of pharmaceutical preparations.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE132907X | 1927-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH132907A true CH132907A (en) | 1929-05-15 |
Family
ID=5664731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH132907D CH132907A (en) | 1927-03-31 | 1928-01-31 | Process for the preparation of a halogenated 2-pyridine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH132907A (en) |
-
1928
- 1928-01-31 CH CH132907D patent/CH132907A/en unknown
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