DE2614827C2 - Verfahren zur Herstellung von 3-Phenylpyridazon-(6) - Google Patents
Verfahren zur Herstellung von 3-Phenylpyridazon-(6)Info
- Publication number
- DE2614827C2 DE2614827C2 DE2614827A DE2614827A DE2614827C2 DE 2614827 C2 DE2614827 C2 DE 2614827C2 DE 2614827 A DE2614827 A DE 2614827A DE 2614827 A DE2614827 A DE 2614827A DE 2614827 C2 DE2614827 C2 DE 2614827C2
- Authority
- DE
- Germany
- Prior art keywords
- ammonium salt
- ammonia
- acid
- acetophenone
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 15
- 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 description 8
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 26
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 26
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 12
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 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 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000012266 salt solution Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 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 description 1
- -1 2-hydroxy-4-oxo-4-phenylbutyric acid ammonium salt Chemical compound 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- KTNLBNLZPDXIKD-UHFFFAOYSA-N carbonic acid 1H-pyrazole Chemical compound OC(O)=O.c1cn[nH]c1 KTNLBNLZPDXIKD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 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
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000003786 synthesis reaction 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)
Priority Applications (4)
| 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) |
| CH358177A CH626071A5 (en) | 1976-03-24 | 1977-03-22 | Process for preparing 3-phenyl-6-pyridazone |
| JP3121477A JPS52116485A (en) | 1976-03-24 | 1977-03-23 | Preparation of 33phenylpyridazonee*6* |
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 (2)
| Publication Number | Publication Date |
|---|---|
| DE2614827A1 DE2614827A1 (de) | 1977-10-20 |
| DE2614827C2 true DE2614827C2 (de) | 1983-01-20 |
Family
ID=25597844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2614827A Expired DE2614827C2 (de) | 1976-03-24 | 1976-04-06 | Verfahren zur Herstellung von 3-Phenylpyridazon-(6) |
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 |
|---|---|
| CH626071A5 (en) | 1981-10-30 |
| JPS52116485A (en) | 1977-09-29 |
| JPS56429B2 (enExample) | 1981-01-08 |
| ATA217076A (de) | 1977-09-15 |
| DE2614827A1 (de) | 1977-10-20 |
| AT343125B (de) | 1978-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3120912A1 (de) | Verfahren zur herstellung von p-nitrophenetol | |
| DE3207746A1 (de) | Verfahren zur herstellung von trimethylolpropan | |
| DE2614827C2 (de) | Verfahren zur Herstellung von 3-Phenylpyridazon-(6) | |
| DE69402556T2 (de) | Herstellung von n-phosphonomethylglysin und derensalze | |
| EP0176026B1 (de) | Verfahren zur Herstellung von 2,4-Dichlor-5-fluor-benzoesäure | |
| EP0057889B1 (de) | Verfahren zur Herstellung von 1-Alkyl-2-chlor-5-nitro-4-benzol-sulfonsäuren | |
| DE2027972A1 (de) | Verfahren zur Herstellung von eckige Klammer auf ,N Bis(cyanmethyl)glycin eckige Klammer zu | |
| DE1146050B (de) | Verfahren zur Herstellung von Fulvenen | |
| DE2202204C2 (de) | Verfahren zur Herstellung von 2-Mercaptobenzimidazol | |
| DE2627223A1 (de) | Verfahren zur herstellung von 4-benzoylpyrazol-derivaten | |
| DE2649744C3 (de) | Verfahren zur Herstellung von Indolin | |
| DE2819798C2 (enExample) | ||
| DE2116159C3 (de) | Verfahren zur Herstellung von 4-Pyridylthio-essigsäure | |
| DE1277244B (de) | Verfahren zur Herstellung von 2, 3-Dibrombuten-(2)-diol-(1,4),2,2,3,3-Tetrabrombutandiol-(1,4) und/oder Mucobromsaeure | |
| DE2065698A1 (de) | Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon | |
| AT308064B (de) | Verfahren zur Herstellung von neuen Sulfoniumverbindungen von α-Hydroxy-γ-alkylmercaptobuttersäuren | |
| DE2256614B2 (de) | Verfahren zur Herstellung von 2-(2-Aminobenzoyl)-pyridinen | |
| AT318634B (de) | Verfahren zur Herstellung von neuem 3-Phenyl-4,5,6-trichlor-pyridazin | |
| AT334379B (de) | Verfahren zur herstellung von neuen 6-aza-3h-1,4-benzodiazepinen und deren salzen | |
| DE2660213C2 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| DE2721374A1 (de) | Verfahren zur herstellung von phosphin | |
| DD214125A1 (de) | Verfahren zur herstellung von n-(beta-cyanethyl)-anilin | |
| DD273253B5 (de) | Verfahren zur Herstellung von 1-(3-Halogenpropyl)-benzimidazolon-2-Derivaten | |
| CH302903A (de) | Verfahren zur Herstellung von Thiosemicarbazonen. | |
| DE1042588B (de) | Verfahren zur Herstellung von ª‡,ª‡-Dichlor-ªŠ-caprolactam |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: AGROLINZ AGRARCHEMIKALIEN MUENCHEN GMBH, 8000 MUEN |