CH210140A - Process for the preparation of a phenanthridine derivative. - Google Patents
Process for the preparation of a phenanthridine derivative.Info
- Publication number
- CH210140A CH210140A CH210140DA CH210140A CH 210140 A CH210140 A CH 210140A CH 210140D A CH210140D A CH 210140DA CH 210140 A CH210140 A CH 210140A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- groups
- amino
- chloride
- nitro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000005053 phenanthridines Chemical class 0.000 title description 3
- 150000003839 salts Chemical group 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- ICKZXHJGSIEAKM-UHFFFAOYSA-N 6-(4-aminophenyl)-5-methylphenanthridin-5-ium-8-amine;chloride Chemical compound [Cl-].C12=CC(N)=CC=C2C2=CC=CC=C2[N+](C)=C1C1=CC=C(N)C=C1 ICKZXHJGSIEAKM-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- NZDXSXLYLMHYJA-UHFFFAOYSA-M 4-[(1,3-dimethylimidazol-1-ium-2-yl)diazenyl]-n,n-dimethylaniline;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1N=NC1=[N+](C)C=CN1C NZDXSXLYLMHYJA-UHFFFAOYSA-M 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 150000003855 acyl compounds Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- KPLILHLLZCRADM-UHFFFAOYSA-N 7-nitro-9-(4-nitrophenyl)phenanthridine Chemical class [N+](=O)([O-])C=1C2=CN=C3C=CC=CC3=C2C=C(C1)C1=CC=C(C=C1)[N+](=O)[O-] KPLILHLLZCRADM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- -1 p-nitrobenzamido Chemical group 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- ZEFVQQCPUILOGN-UHFFFAOYSA-N 9-(4-aminophenyl)phenanthridin-7-amine Chemical compound NC=1C2=CN=C3C=CC=CC3=C2C=C(C1)C1=CC=C(C=C1)N ZEFVQQCPUILOGN-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000654 trypanocidal effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé pour la préparation d'un dérivé de phénanthridine. La présente invention concerne un pro cédé pour la préparation de chiorrure de 7 amino - 9 - (p - aminophényl)-10--méthylphénan- thridinium, qui est un composé trypanocide d'un excellent effet thérapeutique- et qui cristallise en forme de plaque rouge-rubis, fondant (avec décomposition) à 262 C et ayant la formule suivante:
EMI0001.0007
Suivant le procédé pour la préparation de ce dérivé de phénanthridine, on traite de la 7-nitro-9-(p-nitrophényl)-phénanthridine avec un agent réducteur, de façon à réduire les groupes nitmo en groupes amino, puis on acyle les groupes amino et traite le composé acylé avec un agent méthylant, et ayant formé le sel quaternaire sous forme de chlo- rure,
ledit sel est finalement hydrolysé pour éliminer les groupes acyliques.
<I>Exemple:</I> Un mélange de 20 parties en poids de 4'-nitro-2-(p-nitrobenzamido)-diphényle (ob tenu par condensation en pyridine de 4' nitro-2-xénylamine et de chlorure p-nitro- benzoylique) et de 40 parties d'oxychlorure de phosphore est chauffé pendant 30 heures; l'excès d'oxychlorure est éliminé par intro duction prudente de la masse dans de l'eau et le produit solide est recueilli par filtra tion.
En faisant cristalliser ce produit de la pyridine on obtient, en bon rendement, de la 7-nitro-9-(p-nitrophényl)-phénanthridine très pure ayant le point de fusion de 327 C. Par réduction avec de l'hydrogène, .dans un autoclave, à une pression de 5 atmosphères et avec de l'oxyde platinique comme catalyseur, on obtient de la 7-amino-9-(p-aminophényl)- phénanthridine ayant le point de fusion de 212 C.
Ce composé est diacétylé selon la méthode bien connue et le composé diacéty- lique est amené à réagir avec du p-toluène- sulfonate de méthyle dans du nitrobenzène chaud, et, après distillation de ce dernier à la vapeur, un chlorure quaternaire est obtenu sous forme d'aiguilles oranges par précipi tation à. l'aide de chlorure de sodium lors de la liqueur aqueuse;
par hydrolyse de ce sel quaternaire avec de l'acide chlorhydrique modérément. concentré, on obtient le chlorure de 7-amino-9-(p-aminophényl)-10-méthylphé- nanthridinium, qui possède les propriétés signalées plus haut.
Process for the preparation of a phenanthridine derivative. The present invention relates to a process for the preparation of 7 amino - 9 - (p - aminophenyl) -10 - methylphenanthridinium chloride, which is a trypanocidal compound of excellent therapeutic effect and which crystallizes in plaque form. ruby red, melting (with decomposition) at 262 C and having the following formula:
EMI0001.0007
According to the process for the preparation of this phenanthridine derivative, 7-nitro-9- (p-nitrophenyl) -phenanthridine is treated with a reducing agent, so as to reduce the nitmo groups to amino groups, then the groups are acylated. amino and treats the acylated compound with a methylating agent, and having formed the quaternary salt in the form of chloride,
said salt is finally hydrolyzed to remove acyl groups.
<I> Example: </I> A mixture of 20 parts by weight of 4'-nitro-2- (p-nitrobenzamido) -diphenyl (obtained by condensation in pyridine of 4 'nitro-2-xenylamine and of p chloride -nitro-benzoylique) and 40 parts of phosphorus oxychloride is heated for 30 hours; the excess of oxychloride is removed by careful introduction of the mass in water and the solid product is collected by filtration.
By crystallizing this product from pyridine, very pure 7-nitro-9- (p-nitrophenyl) -phenanthridine having the melting point of 327 C. By reduction with hydrogen, is obtained in good yield. in an autoclave at a pressure of 5 atmospheres and with platinum oxide as a catalyst, 7-amino-9- (p-aminophenyl) - phenanthridine having a melting point of 212 C.
This compound is diacetylated according to the well-known method and the diacetyl compound is reacted with methyl p-toluenesulphonate in hot nitrobenzene, and, after steam distillation of the latter, a quaternary chloride is obtained under shaped like orange needles by precipitation. using sodium chloride during the aqueous liquor;
by hydrolysis of this quaternary salt with mild hydrochloric acid. Concentrated, 7-amino-9- (p-aminophenyl) -10-methylphenanthridinium chloride is obtained, which has the properties mentioned above.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB210140X | 1938-01-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210140A true CH210140A (en) | 1940-06-15 |
Family
ID=10155716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210140D CH210140A (en) | 1938-01-13 | 1939-01-05 | Process for the preparation of a phenanthridine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210140A (en) |
-
1939
- 1939-01-05 CH CH210140D patent/CH210140A/en unknown
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