CH634564A5 - Dihydroxy-3,4 dihydro-4,5 phenyl-6 pyridazine et son tautomere l'hydroxy-4 dihydro-4,5 phenyl-6 pyridazone-3 et leur utilisation pour la fabrication de la phenyl-3 pyridazone-6. - Google Patents

Dihydroxy-3,4 dihydro-4,5 phenyl-6 pyridazine et son tautomere l'hydroxy-4 dihydro-4,5 phenyl-6 pyridazone-3 et leur utilisation pour la fabrication de la phenyl-3 pyridazone-6. Download PDF

Info

Publication number: CH634564A5
Authority: CH; Switzerland
Prior art keywords: phenyl; dihydro; pyridazone; dihydroxy; pyridazine
Prior art date: 1977-09-22

Application number

CH979678A

Other languages

English (en)

French (fr)

Inventor

Yani Christidis

Original Assignee

Hoechst France

Priority date (The priority date 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 date listed.)

1977-09-22

Filing date

1978-09-19

Publication date

1983-02-15

1977-09-22 Priority claimed from FR7728647A external-priority patent/FR2408592A1/fr

1977-09-22 Priority claimed from FR7728648A external-priority patent/FR2403998A1/fr

1978-09-19 Application filed by Hoechst France filed Critical Hoechst France

1983-02-15 Publication of CH634564A5 publication Critical patent/CH634564A5/fr

Links

238000004519 manufacturing process Methods 0.000 title claims description 7
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 title claims description 4
WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 title 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
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 9
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 description 5
RGZUOSUGPLWXOQ-UHFFFAOYSA-N 5-hydroxy-3-phenyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)C(O)CC(C=2C=CC=CC=2)=N1 RGZUOSUGPLWXOQ-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 5
239000012429 reaction media Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 7
238000000034 method Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000002609 medium Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000018044 dehydration Effects 0.000 description 4
238000006297 dehydration reaction Methods 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 3
238000005406 washing Methods 0.000 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 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
229910014033 C-OH Inorganic materials 0.000 description 2
229910014570 C—OH Inorganic materials 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
-1 3,4-dihydroxy-4,5-dihydroxy-6-phenyl pyridazine Chemical compound 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical compound OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
229910017849 NH2—NH2 Inorganic materials 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
244000309464 bull Species 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000010902 straw Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
- 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
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
- 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)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH979678A 1977-09-22 1978-09-19 Dihydroxy-3,4 dihydro-4,5 phenyl-6 pyridazine et son tautomere l'hydroxy-4 dihydro-4,5 phenyl-6 pyridazone-3 et leur utilisation pour la fabrication de la phenyl-3 pyridazone-6. CH634564A5 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7728647A FR2408592A1 (fr)	1977-09-22	1977-09-22	Procede de fabrication de la phenyl-3-pyridazone-6
FR7728648A FR2403998A1 (fr)	1977-09-22	1977-09-22	Dihydroxy-3,4 dihydro-4,5 phenyl-6 pyridazine et son tautomere l'hydroxy-4 dihydro-4,5 phenyl-6 pyridazone-3 et leur procede de fabrication

Publications (1)

Publication Number	Publication Date
CH634564A5 true CH634564A5 (fr)	1983-02-15

Family

ID=26220230

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH979678A CH634564A5 (fr)	1977-09-22	1978-09-19	Dihydroxy-3,4 dihydro-4,5 phenyl-6 pyridazine et son tautomere l'hydroxy-4 dihydro-4,5 phenyl-6 pyridazone-3 et leur utilisation pour la fabrication de la phenyl-3 pyridazone-6.

Country Status (4)

Country	Link
AT (1)	AT361936B (de)
CH (1)	CH634564A5 (de)
DE (1)	DE2841421A1 (de)
GB (1)	GB2004873B (de)

1978
- 1978-09-15 AT AT668978A patent/AT361936B/de not_active IP Right Cessation
- 1978-09-19 GB GB7837349A patent/GB2004873B/en not_active Expired
- 1978-09-19 CH CH979678A patent/CH634564A5/fr not_active IP Right Cessation
- 1978-09-22 DE DE19782841421 patent/DE2841421A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
GB2004873B (en)	1982-01-27
AT361936B (de)	1981-04-10
DE2841421A1 (de)	1979-04-05
ATA668978A (de)	1980-09-15
GB2004873A (en)	1979-04-11

Legal Events

Date	Code	Title	Description
1993-05-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
FR2593175A1 (fr)	1987-07-24	Procede de production de 3-phenyl-4-cyanopyrroles.
CH616161A5 (de)	1980-03-14
US4221741A (en)	1980-09-09	Preparation of 4(6'-methoxy-2'-naphthyl)butan-2-one
CH316025A (fr)	1956-09-15	Procédé de préparation de 3,5-diamino-6-aryl-1,2,4-triazines
AU657613B2 (en)	1995-03-16	Process for the preparation of substituted indanones
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US5859296A (en)	1999-01-12	Process for isolating hydroxypivalic acid from aqueous solution
US4720553A (en)	1988-01-19	Method for synthesizing N-aminophthalimide
Manske et al.	1939	A Synthesis of α-Naphthyl-Acetic Acid and Some Homologues
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FR2588869A1 (fr)	1987-04-24	Procede pour la fabrication d'acides alkanoiques
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