CH128367A - Process for the preparation of B-naphtisatin. - Google Patents
Process for the preparation of B-naphtisatin.Info
- Publication number
- CH128367A CH128367A CH128367TA CH128367A CH 128367 A CH128367 A CH 128367A CH 128367T A CH128367T A CH 128367TA CH 128367 A CH128367 A CH 128367A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- naphtisatin
- chloride
- nitrobenzene
- isatin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- JXDYKVIHCLTXOP-UHFFFAOYSA-N Pseudoisatin Natural products C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- RVZFBDVLNFODOM-UHFFFAOYSA-N 3h-benzo[e]indole-1,2-dione Chemical compound C1=CC=CC2=C(C(C(=O)N3)=O)C3=CC=C21 RVZFBDVLNFODOM-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
Description
Verfahren zur Darstellung von f-Napiitisatiii. Gegenstand vorliegender Erfindung ist ein Verfahren zur Darstellung von ss-Napht- isatin; das Verfahren ist dadurch gekenn zeichnet, dass man ein ss-IL aphtyloxamin- säurehalogenid, zum Beispiel ss-Naphtyloxa- minsäurechiorid mit kondensierend wirkenden Mitteln, zum Beispiel mit wasserfreiem Aluminiumchlorid, Eisenchlorid usw., be handelt.
Die Kondensation kann in Gegen wart oder in Abwesenheit von Lösungs- oder Suspensionsmitteln ausgeführt werden.
Das ss-Naplitisatin ist bekannt (siele zum Beispiel Berichte 21. 115).
Beispiel: 50 Gev%Tielitsteile ss-\ap@t@-lo@amins@ure- chlorid vom Schmelzpunkt 114 bis<B>115'</B> werden in 200 Gewichtsteilen Nitrobenzol gelöst und unter Rühren allmählich 5 0 Ge wichtsteile wasserfreies Aluminiumchloricl zugefügt. Die Temperatur beträgt während des Eintragens zweckmässig 40 bis<B>50'</B> und kann zur Beendigung der Reaktion schliesslich auf etwa 80 gesteigert werden.
Wenn eine Probe nach dem Abblasen des Lösungsmittels in verdünnter Natronlauge vollkommen löslich ist, wird auf Eis ge gossen und das Nitrobenzol mit Wasser- dampf abdestilliert. Das Isatin bleibt in Form einer dunkelroten kristallinischen Masse zurück und kann auf dem üblichen Wege gereinigt werden. Die Ausbeute beträgt<B>75</B> bis 80 % der Theorie.
Method for the presentation of f-Napiitisatiii. The present invention relates to a process for the preparation of ss-naphthisatin; the process is characterized in that an ß-IL aphtyloxamic acid halide, for example ß-naphtyloxamic acid chloride, is treated with agents having a condensing effect, for example with anhydrous aluminum chloride, iron chloride, etc.
The condensation can be carried out in the presence or absence of solvents or suspending agents.
The ss-naplitisatin is known (see for example reports 21. 115).
Example: 50 Gev% Tielitsteile ss- \ ap @ t @ -lo @ amins @ ure- chloride with a melting point of 114 to 115 'are dissolved in 200 parts by weight of nitrobenzene and gradually 50 parts by weight of anhydrous aluminum chloricl with stirring added. The temperature is expediently 40 to 50 'during the introduction and can finally be increased to about 80 to end the reaction.
If a sample is completely soluble in dilute sodium hydroxide solution after the solvent has been blown off, it is poured onto ice and the nitrobenzene is distilled off with steam. The isatin remains in the form of a dark red crystalline mass and can be purified in the usual way. The yield is <B> 75 </B> to 80% of theory.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH128367T CH128367A (en) | 1927-02-02 | 1927-02-02 | Process for the preparation of B-naphtisatin. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH128367T CH128367A (en) | 1927-02-02 | 1927-02-02 | Process for the preparation of B-naphtisatin. |
| CH125716T | 1927-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH128367A true CH128367A (en) | 1928-10-16 |
Family
ID=25710543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH128367T CH128367A (en) | 1927-02-02 | 1927-02-02 | Process for the preparation of B-naphtisatin. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH128367A (en) |
-
1927
- 1927-02-02 CH CH128367T patent/CH128367A/en unknown
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