BE515460A - - Google Patents
Info
- Publication number
- BE515460A BE515460A BE515460DA BE515460A BE 515460 A BE515460 A BE 515460A BE 515460D A BE515460D A BE 515460DA BE 515460 A BE515460 A BE 515460A
- Authority
- BE
- Belgium
- Prior art keywords
- methoxybenzaldehyde
- isonicotin
- pyridoylhydrazone
- pyridoylhydrazide
- product
- Prior art date
Links
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 231100000111 LD50 Toxicity 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001549 tubercolostatic effect Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- MYEHAWYWNFNHPT-UHFFFAOYSA-N n-[(4-methoxyphenyl)methylideneamino]pyridine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1C=NNC(=O)C1=CC=NC=C1 MYEHAWYWNFNHPT-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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
<Desc/Clms Page number 1> PROCEDE DE PREPARATION DE LA 4-PYRIDOYLHYDRAZONE DE P-METHOXYBENZALDEHYDE. Il est connu que l'hydrazide isonicotinique possède des proprié- tés tuberculostatiques très marquées. Ce produit présente toutefois une toxi- cité non négligeable : la dose létale 50% (L. D.50) sur la souris de 20 gram- mes est de 5 milligrammes. On a également constaté que certaines hydrazones isonicotiniques possèdent une action tuberculostatique plus élevée que celle de l'hydrazide isonicotinique. La présente invention se rapporte à un procédé de préparation de la 4-pyridoylhydrazone de p-méthoxybenzaldéhyde par réaction entre la 4- pyridoylhydrazide et le p-méthoxy-benzaldéhyde selon Inéquation EMI1.1 1/intérêt de ce produit nouveau réside dans le fait qu'il mon- tre la haute activité des hydrazones déjà connues et qu'il possède une toxi- cité particulièrement faible : L. D.50 pour une souris de 20 grammes est de 80 milligrammes pour le chlorhydrate. Exemple. On chauffe des parts égales de 4-pyridoylhydrazide et de p-mé- thoxybenzaldéhyde intimement mélangées de manière à obtenir une solution lim- <Desc/Clms Page number 2> pide. La réaction est assez violente. On continue à chauffer pendant quel- ques minutes, on laisse légèrement refroidir et on ajoute 2 à 3 volumes d'al- cool éthylique bouillant. On triture la masse cristalline formée et on fil- tre à chaud. Le produit est lavé avec un peu d'alcool et séché. Recristalli- sédans l'alcool éthylique à 94 , il fond à 170 C. Son chlorhydrate peut tre obtenu par dissolution de 15 g du produit dans 300 cm3 d'alcool éthyli- que à 94 porté à ébullition et par addition d'un excès d'HCl en solution alcoolique ou éthérée. Le monochlorhydrate précipite sous forme de petits cristaux jaunes qu'on filtre et sèche sous vide.
Claims (1)
- RESUME - REVENDICATIONS.1 Procédé de préparation de la 4-pyridoylbydrazone de p-métho- xybenzaldéhyde, caractérisé en ce que l'on fait réagir, en le chauffant, un mélange de parties égales de 4-pyridoylhydrazide et de p-méthoxybenzaldébyde.2 La 4-pyridoylhydrazone de p-méthoxybenzaldébyde en tant que produit chimique nouveau.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE515460A true BE515460A (fr) |
Family
ID=152957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE515460D BE515460A (fr) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE515460A (fr) |
-
0
- BE BE515460D patent/BE515460A/fr unknown
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