CH639958A5 - Process for the preparation of 3-phenyl-6-pyridazone - Google Patents
Process for the preparation of 3-phenyl-6-pyridazone Download PDFInfo
- Publication number
- CH639958A5 CH639958A5 CH400379A CH400379A CH639958A5 CH 639958 A5 CH639958 A5 CH 639958A5 CH 400379 A CH400379 A CH 400379A CH 400379 A CH400379 A CH 400379A CH 639958 A5 CH639958 A5 CH 639958A5
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- hydroxy
- hydrazine
- reaction
- pyridazone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 4
- 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 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 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 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000002609 medium Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 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 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- HIYZFFZORGXZTL-UHFFFAOYSA-N 2-benzoylprop-2-enoic acid Chemical group OC(=O)C(=C)C(=O)C1=CC=CC=C1 HIYZFFZORGXZTL-UHFFFAOYSA-N 0.000 description 2
- TVKFDBOFBKXOQT-UHFFFAOYSA-N 5-phenyl-1h-pyridazin-6-one Chemical class O=C1NN=CC=C1C1=CC=CC=C1 TVKFDBOFBKXOQT-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical class OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 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
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010792 warming 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
- C07D237/16—Two oxygen atoms
-
- 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 |
|---|---|---|---|
| DE19782819798 DE2819798A1 (de) | 1978-05-05 | 1978-05-05 | Verfahren zur herstellung von 3-phenyl-pyridazon-(6) |
| AT336778A AT357547B (de) | 1978-05-05 | 1978-05-10 | Verfahren zur herstellung von 3-phenyl- pyridazon-(6) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH639958A5 true CH639958A5 (en) | 1983-12-15 |
Family
ID=25599937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH400379A CH639958A5 (en) | 1978-05-05 | 1979-04-27 | Process for the preparation of 3-phenyl-6-pyridazone |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5928547B2 (enrdf_load_stackoverflow) |
| AT (1) | AT357547B (enrdf_load_stackoverflow) |
| CH (1) | CH639958A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2819798A1 (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0101156A3 (en) * | 1982-06-24 | 1984-08-22 | Smith Kline & French Laboratories Limited | Process for preparing 6-(2-hydroxyphenyl)-3-pyridazinone |
| JPS63278604A (ja) * | 1987-05-11 | 1988-11-16 | Nippon Steel Corp | カリバ−ロ−ルのオンライン研摩方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1105281A (en) * | 1965-03-03 | 1968-03-06 | Seperic | Improvements in and relating to new pyridazone derivatives and process for preparing same |
| AT330195B (de) * | 1974-07-30 | 1976-06-25 | Chemie Linz Ag | Verfahren zur herstellung von phenylpyridazonen |
| AT343125B (de) * | 1976-03-24 | 1978-05-10 | Chemie Linz Ag | Verfahren zur herstellung von 3-phenylpyridazon- (6) |
-
1978
- 1978-05-05 DE DE19782819798 patent/DE2819798A1/de active Granted
- 1978-05-10 AT AT336778A patent/AT357547B/de not_active IP Right Cessation
-
1979
- 1979-04-27 CH CH400379A patent/CH639958A5/de not_active IP Right Cessation
- 1979-05-02 JP JP54053546A patent/JPS5928547B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA336778A (de) | 1979-12-15 |
| JPS54145685A (en) | 1979-11-14 |
| JPS5928547B2 (ja) | 1984-07-13 |
| AT357547B (de) | 1980-07-10 |
| DE2819798C2 (enrdf_load_stackoverflow) | 1989-02-16 |
| DE2819798A1 (de) | 1979-11-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |