BE516994A - - Google Patents
Info
- Publication number
- BE516994A BE516994A BE516994DA BE516994A BE 516994 A BE516994 A BE 516994A BE 516994D A BE516994D A BE 516994DA BE 516994 A BE516994 A BE 516994A
- Authority
- BE
- Belgium
- Prior art keywords
- phthalazine
- amino
- parts
- volume
- hydrazine
- Prior art date
Links
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- WTYSCLHDMXBMKM-UHFFFAOYSA-N phthalazin-1-amine Chemical class C1=CC=C2C(N)=NN=CC2=C1 WTYSCLHDMXBMKM-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- AQHQGNYQXCIWDG-UHFFFAOYSA-N 4-methylphthalazin-1-amine Chemical compound C1=CC=C2C(C)=NN=C(N)C2=C1 AQHQGNYQXCIWDG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 3
- 230000001034 aminogenic Effects 0.000 claims description 2
- 150000002429 hydrazines Chemical class 0.000 claims description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- GZHRIJILPSVIKI-UHFFFAOYSA-N 1-chloro-4-piperidin-1-ylphthalazine Chemical compound C12=CC=CC=C2C(Cl)=NN=C1N1CCCCC1 GZHRIJILPSVIKI-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N Pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XAJLIPKOOUAUFK-UHFFFAOYSA-N (4-methylphthalazin-1-yl)hydrazine Chemical compound C1=CC=C2C(C)=NN=C(NN)C2=C1 XAJLIPKOOUAUFK-UHFFFAOYSA-N 0.000 description 1
- ODCNAEMHGMYADO-UHFFFAOYSA-N 1,4-dichlorophthalazine Chemical compound C1=CC=C2C(Cl)=NN=C(Cl)C2=C1 ODCNAEMHGMYADO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IEDBAGGSOLFBBH-UHFFFAOYSA-N 1-chloro-4-methylphthalazine Chemical compound C1=CC=C2C(C)=NN=C(Cl)C2=C1 IEDBAGGSOLFBBH-UHFFFAOYSA-N 0.000 description 1
- -1 1-isobutylamino - Chemical class 0.000 description 1
- YTDZFWNQRRMELI-UHFFFAOYSA-N 6-phenylpyridazin-3-amine Chemical compound N1=NC(N)=CC=C1C1=CC=CC=C1 YTDZFWNQRRMELI-UHFFFAOYSA-N 0.000 description 1
- KDSNLYIMUZNERS-UHFFFAOYSA-N Isobutylamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- AQKDJGAPGQAXIY-UHFFFAOYSA-N phthalazine-1,4-diamine Chemical compound C1=CC=C2C(N)=NN=C(N)C2=C1 AQKDJGAPGQAXIY-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical class NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/34—Phthalazines with nitrogen atoms directly attached to carbon atoms of the nitrogen-containing ring, e.g. hydrazine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE516994A true BE516994A (de) |
Family
ID=154018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE516994D BE516994A (de) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE516994A (de) |
-
0
- BE BE516994D patent/BE516994A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH469659A (fr) | Procédé d'obtention de dérivés du tri-hydroxy-méthyl-aminométhane | |
| CA1312333C (fr) | Sel de strontium, son procede de preparation et les compositions pharmaceutiques le renfermant | |
| BE516994A (de) | ||
| CH316025A (fr) | Procédé de préparation de 3,5-diamino-6-aryl-1,2,4-triazines | |
| CH573386A5 (en) | Para-Isobutyl-phenyl-butyric acid prepn. - from corresp. acetonitrile cpd., having antiinflammatory, analgesic and antipyretic activity | |
| BE516993A (de) | ||
| BE528076A (de) | ||
| BE521436A (de) | ||
| BE528490A (de) | ||
| BE509974A (de) | ||
| FR2473512A1 (fr) | Nouveaux 2-aminomethyl-6-halogeno-phenols, leur preparation et leur application comme medicaments | |
| BE517270A (de) | ||
| BE721781A (de) | ||
| BE520959A (de) | ||
| BE577413A (de) | ||
| BE524378A (de) | ||
| BE517764A (de) | ||
| BE553657A (de) | ||
| BE636257A (de) | ||
| BE534468A (de) | ||
| BE522203A (de) | ||
| BE531553A (de) | ||
| BE520816A (de) | ||
| BE435094A (de) | ||
| BE425248A (de) |