CH626071A5 - Process for preparing 3-phenyl-6-pyridazone - Google Patents
Process for preparing 3-phenyl-6-pyridazone Download PDFInfo
- Publication number
- CH626071A5 CH626071A5 CH358177A CH358177A CH626071A5 CH 626071 A5 CH626071 A5 CH 626071A5 CH 358177 A CH358177 A CH 358177A CH 358177 A CH358177 A CH 358177A CH 626071 A5 CH626071 A5 CH 626071A5
- Authority
- CH
- Switzerland
- Prior art keywords
- ammonium salt
- hydroxy
- oxo
- reaction
- ammonia
- Prior art date
Links
- IJUIPRDMWWBTTQ-UHFFFAOYSA-N 3-phenyl-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(C=2C=CC=CC=2)=N1 IJUIPRDMWWBTTQ-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 47
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 28
- COFAOIWBTJSSPD-UHFFFAOYSA-N 2-hydroxy-4-oxo-4-phenylbutanoic acid Chemical compound OC(=O)C(O)CC(=O)C1=CC=CC=C1 COFAOIWBTJSSPD-UHFFFAOYSA-N 0.000 claims abstract description 22
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims abstract description 21
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 20
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 6
- 230000002411 adverse Effects 0.000 claims abstract description 3
- 239000006227 byproduct Substances 0.000 claims abstract description 3
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims abstract description 3
- 239000011814 protection agent Substances 0.000 claims abstract description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 34
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000012266 salt solution Substances 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 238000001256 steam distillation Methods 0.000 claims description 3
- PLPDHGOODMBBGN-VOTSOKGWSA-N (e)-4-oxo-4-phenylbut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)C1=CC=CC=C1 PLPDHGOODMBBGN-VOTSOKGWSA-N 0.000 claims description 2
- TVKFDBOFBKXOQT-UHFFFAOYSA-N 5-phenyl-1h-pyridazin-6-one Chemical compound O=C1NN=CC=C1C1=CC=CC=C1 TVKFDBOFBKXOQT-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 claims description 2
- 231100000989 no adverse effect Toxicity 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract 1
- -1 2-hydroxy-4-oxo-4-phenylbutyric acid ammonium salt Chemical compound 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000926 separation method Methods 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
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D237/14—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT217076A AT343125B (de) | 1976-03-24 | 1976-03-24 | Verfahren zur herstellung von 3-phenylpyridazon- (6) |
| DE2614827A DE2614827C2 (de) | 1976-03-24 | 1976-04-06 | Verfahren zur Herstellung von 3-Phenylpyridazon-(6) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626071A5 true CH626071A5 (en) | 1981-10-30 |
Family
ID=25597844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH358177A CH626071A5 (en) | 1976-03-24 | 1977-03-22 | Process for preparing 3-phenyl-6-pyridazone |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS52116485A (enExample) |
| AT (1) | AT343125B (enExample) |
| CH (1) | CH626071A5 (enExample) |
| DE (1) | DE2614827C2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2819798A1 (de) * | 1978-05-05 | 1979-11-08 | Lentia Gmbh | Verfahren zur herstellung von 3-phenyl-pyridazon-(6) |
| DE3226768A1 (de) * | 1981-11-05 | 1983-05-26 | Hoechst Ag, 6230 Frankfurt | Derivate der cis, endo-2-azabicyclo-(3.3.0)-octan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung |
| EP0101156A3 (en) * | 1982-06-24 | 1984-08-22 | Smith Kline & French Laboratories Limited | Process for preparing 6-(2-hydroxyphenyl)-3-pyridazinone |
| GR82072B (enExample) * | 1983-05-11 | 1984-12-13 | Byk Gulden Lomberg Chem Fab |
-
1976
- 1976-03-24 AT AT217076A patent/AT343125B/de not_active IP Right Cessation
- 1976-04-06 DE DE2614827A patent/DE2614827C2/de not_active Expired
-
1977
- 1977-03-22 CH CH358177A patent/CH626071A5/de not_active IP Right Cessation
- 1977-03-23 JP JP3121477A patent/JPS52116485A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52116485A (en) | 1977-09-29 |
| JPS56429B2 (enExample) | 1981-01-08 |
| ATA217076A (de) | 1977-09-15 |
| DE2614827C2 (de) | 1983-01-20 |
| DE2614827A1 (de) | 1977-10-20 |
| AT343125B (de) | 1978-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |