CH287867A - Process for the preparation of 5-oxy-benz (cd) indoline. - Google Patents
Process for the preparation of 5-oxy-benz (cd) indoline.Info
- Publication number
- CH287867A CH287867A CH287867DA CH287867A CH 287867 A CH287867 A CH 287867A CH 287867D A CH287867D A CH 287867DA CH 287867 A CH287867 A CH 287867A
- Authority
- CH
- Switzerland
- Prior art keywords
- indoline
- benz
- oxy
- preparation
- absorption spectrum
- Prior art date
Links
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 4
- 238000000862 absorption spectrum Methods 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LRELZHZTPKWCPR-UHFFFAOYSA-N COC=1C=CC=2CN(C3=CC=CC=1C=23)C(C)=O Chemical compound COC=1C=CC=2CN(C3=CC=CC=1C=23)C(C)=O LRELZHZTPKWCPR-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 5-Oxy-benz(ed) indolin. In der Patentschrift Nr. 282383 ist ein Verfahren zur Herstellung von 5-Metlioxy- N-acetyl-benz(ed)indolin beschrieben.
Die vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung von 5-Oxy- benz (cd) indolin, welches dadurch gekennzeich net ist, dass man ein 5-Alkoxy-N-aeyl-benz- (ed)indolin unter Erhitzen hydrolysiert. Das Absorptionsspektrum einer alkoholischen Lö sung des neuen Stoffes weist bei 335 und bei 405 m,u Maxima auf.
Als hydrolytisch wirkende Reagenzien ha ben sieh Halogenwasserstoffsäuren gut be währt; man verwendet vorzugsweise Brom wasserstoffsäure in siedendem Eisessig.
Das neue Zwischenprodukt soll für die Herstellung von Heilmitteln verwendet wer den.
<I>Beispiel:</I> 5 g 5-Methoxy - N - acetyl-benz (cd) indolin werden in einer Mischung von 40 em3 48- prozentiger Bromwasserstoffsäure und 40 cm3 Eisessig während 11/2 Stunden unter Rück fluss gekocht.
Nach längerem Stehen bei -15 wird das ausgeschiedene Hydrobromid vom 5-Oxy-benz(ed)indolin abfiltriert. Es bildet gelbe Kristalle, welche im zugeschmolzenen Röhrchen bei 234 bis 235 unter Zersetzung schmelzen, und kann durch Umkristallisieren aus 2n-Bromwasserstoffsäure gereinigt wer den. Durch Behandlung mit einer wässerigen Lösung von Silbersulfat kann daraus das Sul fat hergestellt werden.
Die freie Base kann folgendermassen iso liert werden: 2 Gewichtsteile Hydrobromid werden in 25 Volumteilen ln-Salzsäure ge löst. Bei ungefähr 60 wird mit einer ge sättigten Lösung von Natriumacetat versetzt, bis keine weitere Fällung mehr entsteht. Nach Abkühlen auf 0 wird das in Form von hell gelben Kristallen ausgeschiedene 5-Oxy-benz- (cd)indolin abfiltriert. Das Absorptionsspek trum einer alkoholischen Lösung weist bei 335 und 405 mu Maxima auf.
Process for the preparation of 5-oxy-benz (ed) indoline. Patent specification No. 282383 describes a process for the preparation of 5-metlioxy-N-acetyl-benz (ed) indoline.
The present invention relates to a process for the preparation of 5-oxybenz (cd) indoline, which is characterized in that a 5-alkoxy-N-aeyl-benz- (ed) indoline is hydrolyzed with heating. The absorption spectrum of an alcoholic solution of the new substance shows maxima at 335 and 405 m u.
As hydrolytically acting reagents have ben see hydrohalic acids well be; it is preferred to use hydrobromic acid in boiling glacial acetic acid.
The new intermediate is to be used in the manufacture of medicinal products.
<I> Example: </I> 5 g of 5-methoxy - N - acetyl-benz (cd) indoline are refluxed in a mixture of 40 em3 of 48 percent hydrobromic acid and 40 cm3 of glacial acetic acid for 11/2 hours.
After standing for a long time at -15, the precipitated hydrobromide is filtered off from the 5-oxy-benz (ed) indoline. It forms yellow crystals, which melt in the closed tube at 234 to 235 with decomposition, and can be purified by recrystallization from 2N hydrobromic acid. Sul fat can be produced from it by treatment with an aqueous solution of silver sulfate.
The free base can be isolated as follows: 2 parts by weight of hydrobromide are dissolved in 25 parts by volume of ln hydrochloric acid. At about 60 a saturated solution of sodium acetate is added until no further precipitation occurs. After cooling to 0, the 5-oxy-benz- (cd) indoline which separated out in the form of light yellow crystals is filtered off. The absorption spectrum of an alcoholic solution shows maxima at 335 and 405 mu.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH287867T | 1950-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH287867A true CH287867A (en) | 1952-12-31 |
Family
ID=4485978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH287867D CH287867A (en) | 1950-03-11 | 1950-03-11 | Process for the preparation of 5-oxy-benz (cd) indoline. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH287867A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE958648C (en) * | 1953-07-30 | 1957-02-21 | Sandoz Ag | Process for the preparation of 4,5-dihydro-9-carbaethoxy-indolo- (4,3-f, g) -quinoline |
-
1950
- 1950-03-11 CH CH287867D patent/CH287867A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE958648C (en) * | 1953-07-30 | 1957-02-21 | Sandoz Ag | Process for the preparation of 4,5-dihydro-9-carbaethoxy-indolo- (4,3-f, g) -quinoline |
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