NO155578B - PROCEDURE FOR PREPARATION OF 4-CHLORO-5-AMINO-2-PHENYL-3 (2H) -PYRIDAZINON FROM 4,5-DICHLOR-2-PHENYL-3 (2H) -PYRIDAZINON AND AMMONIA. - Google Patents
PROCEDURE FOR PREPARATION OF 4-CHLORO-5-AMINO-2-PHENYL-3 (2H) -PYRIDAZINON FROM 4,5-DICHLOR-2-PHENYL-3 (2H) -PYRIDAZINON AND AMMONIA. Download PDFInfo
- Publication number
- NO155578B NO155578B NO81811077A NO811077A NO155578B NO 155578 B NO155578 B NO 155578B NO 81811077 A NO81811077 A NO 81811077A NO 811077 A NO811077 A NO 811077A NO 155578 B NO155578 B NO 155578B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- pyridazinone
- chloro
- amino
- ammonia
- Prior art date
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 title claims description 30
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 title claims description 27
- VKWCOHVAHQOJGU-UHFFFAOYSA-N 4,5-dichloro-2-phenylpyridazin-3-one Chemical compound O=C1C(Cl)=C(Cl)C=NN1C1=CC=CC=C1 VKWCOHVAHQOJGU-UHFFFAOYSA-N 0.000 title claims description 15
- 229910021529 ammonia Inorganic materials 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 7
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims description 6
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000012452 mother liquor Substances 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- HAKJEHJYRKVCIU-UHFFFAOYSA-N 4-amino-5-chloro-2-phenylpyridazin-3-one Chemical compound O=C1C(N)=C(Cl)C=NN1C1=CC=CC=C1 HAKJEHJYRKVCIU-UHFFFAOYSA-N 0.000 claims description 3
- YLKCHWCYYNKADS-UHFFFAOYSA-N 5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=CC2=C1S(O)(=O)=O YLKCHWCYYNKADS-UHFFFAOYSA-N 0.000 claims description 3
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- LUMLZKVIXLWTCI-IHWYPQMZSA-N (z)-2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(\Cl)C=O LUMLZKVIXLWTCI-IHWYPQMZSA-N 0.000 description 1
- VJWXIRQLLGYIDI-UHFFFAOYSA-N 4,5-dichloro-1h-pyridazin-6-one Chemical class OC1=NN=CC(Cl)=C1Cl VJWXIRQLLGYIDI-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Foreliggende oppfinnelse angår en fremgangsmåte for fremstilling av 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon fra 4,5-diklor-2-fenyl-3.(2H)-pyridazinon og ammoniakk. The present invention relates to a process for the production of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone from 4,5-dichloro-2-phenyl-3.(2H)-pyridazinone and ammonia.
4-klor-5-amino-2-fenyl-3(2H)-pyridazinon er et selektivt virkende herbicid, særlig for anvendelse i sukkerroe-åkre. Sukkerroer viser spesiell motstand mot denne forbindelse. 4- klor-5-amino-2-fenyl-3(2H)-pyridazinon har hittil vært frem-stilt fra 2,3-diklor-4-okso-2-butensyre via omsetning med fenylhydrazih for fremstilling av diklorpyridazinon-derivatet (4,5-diklor-2-fenyl-3(2H)-pyridazinon) som derefter omsettes med ammoniakk under trykk og ved forhøyet temperatur for fremstilling av det ønskede 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon. I dette siste reaksjonstrinn dannes ca. 10-20% av den isomere forbindelse, 4-amino-5-klor-2-fenyl-3(2H)-pyridazinon, som har. bare halvparten av den herbicide virkning som 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon har. 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone is a selectively active herbicide, particularly for use in sugar beet fields. Sugar beet shows particular resistance to this compound. 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone has so far been prepared from 2,3-dichloro-4-oxo-2-butenoic acid via reaction with phenylhydrazide to produce the dichloropyridazinone derivative (4 ,5-dichloro-2-phenyl-3(2H)-pyridazinone) which is then reacted with ammonia under pressure and at elevated temperature to produce the desired 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone . In this last reaction step, approx. 10-20% of the isomeric compound, 4-amino-5-chloro-2-phenyl-3(2H)-pyridazinone, which has. only half the herbicidal effect of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone.
Tysk patent 1.105.232 beskriver fremstilling av 4-klor-5- amino-2-fenyl-3(2H)-pyridazinon fra 4,5-diklor-2-fenyl-3(2H)-pyridazinon og ammoniakk. 4-klor-5-amino-2-fenyl-3 (211)-pyridazinon isoleres i et 64% utbytte fra reaksjonsproduktet sammen med et 10% utbytte av det isomere produkt. German patent 1,105,232 describes the preparation of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone from 4,5-dichloro-2-phenyl-3(2H)-pyridazinone and ammonia. 4-chloro-5-amino-2-phenyl-3 (211)-pyridazinone is isolated in a 64% yield from the reaction product together with a 10% yield of the isomeric product.
Tysk off.skrift 2.100.685 angir at det rå reaksjonsprodukt fra omsetningen beskrevet i tysk patent 1.105.232 inneholder 80% av 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon og 20% av den isomere forbindelse og gir anvisninger for isolering'av rent 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon fra denne blanding ved ekstraksjon med visse oppløsningsmidler. German official publication 2,100,685 states that the crude reaction product from the reaction described in German patent 1,105,232 contains 80% of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone and 20% of the isomeric compound and gives directions for the isolation of pure 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone from this mixture by extraction with certain solvents.
Tsjekkoslovakisk patent 158.843 beskriver fremstilling av 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon ved å føre ammoniakk inn i smeltet 4,5-diklor-2-fenyl-3(2H)-pyridazinon ved 208-220°C. Et 93% rent produkt oppnås i et 71% utbytte. Czechoslovak patent 158,843 describes the preparation of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone by passing ammonia into molten 4,5-dichloro-2-phenyl-3(2H)-pyridazinone at 208- 220°C. A 93% pure product is obtained in a 71% yield.
Det er ikke kjent noen metode for omsetning av 4,5-diklor-2-fenyl-3(2H)-pyridazinon med ammoniakk som gir rent 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon i høyt utbytte. No method is known for the reaction of 4,5-dichloro-2-phenyl-3(2H)-pyridazinone with ammonia which gives pure 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone in high dividend.
Foreliggende oppfinnelse tilveiebringer en fremgangsmåte ved hvilken 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon fremstilles i høyt utbytte og tilnærmet fritt for 4-amino-5-klor-2-fenyl-3(2H)-pyridazinon. Fremgangsmåten, ifølge oppfinnelsen omfatter at 4,5-diklor-2-fenyl-3(2H)-pyridazinon omsettes med vandig ammoniakk i nærvær av en katalysator valgt fra 4-hydroksy-fenyl-eddiksyre, 4-hydroksy-benzoesyre, 1-fenol-4-sulfonsyre, 3-hydroksy-2-pyridon, 3-hydroksypyridin og 1-naftol-5-sulfon-syre. Denne katalysator er i stand til å utskifte selektivt 5-kloratomet i 4,5-diklor-2-fenyl-3(2H)-pyridazinon med en utgående gruppe av en slik natur at det resulterende mellom-produkt er i stand til å alkylere ammoniakk til 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon i høyt utbytte i reaksjonsmediet, med regenerering av katalysatoren. The present invention provides a method by which 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone is produced in high yield and almost free of 4-amino-5-chloro-2-phenyl-3(2H)- pyridazinone. The method according to the invention comprises that 4,5-dichloro-2-phenyl-3(2H)-pyridazinone is reacted with aqueous ammonia in the presence of a catalyst selected from 4-hydroxy-phenyl-acetic acid, 4-hydroxy-benzoic acid, 1-phenol -4-sulfonic acid, 3-hydroxy-2-pyridone, 3-hydroxypyridine and 1-naphthol-5-sulfonic acid. This catalyst is capable of selectively replacing the 5-chloro atom of 4,5-dichloro-2-phenyl-3(2H)-pyridazinone with a leaving group of such a nature that the resulting intermediate is capable of alkylating ammonia to 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone in high yield in the reaction medium, with regeneration of the catalyst.
Forholdet mellom utgangsmaterialet 4,5-diklor-2-fenyl-3(2H)-pyridazon og katalysatoren er fortrinnsvis fra 50:1 The ratio between the starting material 4,5-dichloro-2-phenyl-3(2H)-pyridazone and the catalyst is preferably from 50:1
til 2:1, beregnet på molbasis. to 2:1, calculated on a molar basis.
Omsetningen omfatter anvendelse av 1 mol ammoniakk pr. The turnover includes the use of 1 mol of ammonia per
mol 4,5-diklor-2-fenyl-3(2H)-pyridazinon og 1 mol av et alkalisk middel for nøytralisering av den dannede HC1; og det er således passende å anvende minst 2 mol ammoniakk pr. mol 4,5-diklor-2-fenyl-3(2H)-pyridazinon, og molforholdet mellom ammoniakk og utgangsmaterialet kan være i området 2,1:1 til 10:1. mol of 4,5-dichloro-2-phenyl-3(2H)-pyridazinone and 1 mol of an alkaline agent to neutralize the HCl formed; and it is thus appropriate to use at least 2 mol of ammonia per moles of 4,5-dichloro-2-phenyl-3(2H)-pyridazinone, and the molar ratio of ammonia to starting material may be in the range of 2.1:1 to 10:1.
Ammoniakken kan anvendes som en konsentrert, vandig oppløsning eller som en mer fortynnet vandig oppløsning. The ammonia can be used as a concentrated, aqueous solution or as a more diluted aqueous solution.
Fremgangsmåten ifølge oppfinnelsen kan utføres i et The method according to the invention can be carried out in a
lukket kar, ved moderate trykk, og ved temperaturer mellom ca. 50°C og 150°C under omrøring. closed vessel, at moderate pressures, and at temperatures between approx. 50°C and 150°C with stirring.
Ved reaksjonens begynnelse er reaksjonsblandingen en oppslemning av 4,5-diklor-2-fenyl-3(2H)-pyridazinon, og ved slutten av reaksjonen er reaksjonsblandingen en oppslemning av det dannede 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon . Under omsetningen er reaksjonskomponentene delvis oppløselige eller dispergerbare i reaksjonsmediet. At the beginning of the reaction, the reaction mixture is a slurry of 4,5-dichloro-2-phenyl-3(2H)-pyridazinone, and at the end of the reaction, the reaction mixture is a slurry of the formed 4-chloro-5-amino-2-phenyl-3 (2H)-pyridazinone . During the reaction, the reaction components are partially soluble or dispersible in the reaction medium.
Sluttproduktet isoleres ved filtrering efter omsetningen, vaskes med vann og.tørres. The final product is isolated by filtration after the reaction, washed with water and dried.
Et trekk ved foreliggende oppfinnelse er å tilveiebringe en enkel "one pot" metode, ved hvilken reaks jonsoppløsningen. inneholdende ammoniakk og katalysator, efter isolering av 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon, kan anvendes påny flere ganger. I henhold til dette trekk anvendes, moderluten pluss vaskevann som reaksjonsmedium for neste sats efter isolering av produktet ved filtrering. Derved anvendes katalysatoren påny, og tapet av 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon som skyldes dets oppløselighet i reaksjonsmediet, reduseres. A feature of the present invention is to provide a simple "one pot" method, by which the react ion solution. containing ammonia and catalyst, after isolation of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone, can be reused several times. According to this feature, the mother liquor plus washing water is used as the reaction medium for the next batch after isolation of the product by filtration. Thereby, the catalyst is used again, and the loss of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone, which is due to its solubility in the reaction medium, is reduced.
Det foretrekkes at mengden av reaksjonsmedium som holdes tilbake i filterkaken, erstattes med en tilsvarende mengde vaskevann og føres tilbake til reaksjonsmediet. It is preferred that the amount of reaction medium retained in the filter cake is replaced with a corresponding amount of washing water and returned to the reaction medium.
Fremgangsmåten ifølge oppfinnelsen illustreres i de følgende eksempler: The method according to the invention is illustrated in the following examples:
Eksempel 1 Example 1
4,5-diklor-2-fenyl-pyridazinon (2,41 g), 4-hydroksyfeny1-eddiksyre (1,0 g) og 20% vandig ammoniakk (20 ml) ble oppvarmet til 100-110°C under omrøring i en liten autoklav i 4 timer. Reaksjonsblandingen ble derefter avkjølt til romtemperatur, og det resulterende bunnfall av 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon ble isolert ved filtrering, vasket med vann og tørret. 1,86 g rent 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon ble oppnådd, sm.p. 206-207°C. Moderluten og vaskevæskene inne-holdt 0,15 g 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon. Den totale mengde av dannet 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon var således 2,01 g (91%) . 4,5-dichloro-2-phenyl-pyridazinone (2.41 g), 4-hydroxyphenyl-acetic acid (1.0 g) and 20% aqueous ammonia (20 ml) were heated to 100-110°C with stirring in a small autoclave for 4 hours. The reaction mixture was then cooled to room temperature, and the resulting precipitate of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone was isolated by filtration, washed with water and dried. 1.86 g of pure 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone were obtained, m.p. 206-207°C. The mother liquor and the washing liquids contained 0.15 g of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone. The total amount of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone formed was thus 2.01 g (91%).
Eksempel 2 Example 2
4,5-diklor-2-fenyl-pyridazinon (12,0 g), 4-hydroksy-benzoesyre (3,5 g), vann (75 ml) og 20% vandig ammoniakk (25 ml) ble oppvarmet til 145-150°C under omrøring i en glassautoklav i 5 timer. 4,5-dichloro-2-phenyl-pyridazinone (12.0 g), 4-hydroxy-benzoic acid (3.5 g), water (75 ml) and 20% aqueous ammonia (25 ml) were heated to 145-150 °C with stirring in a glass autoclave for 5 hours.
Reaksjonsblandingen ble derefter avkjølt til romtemperatur, og det resulterende bunnfall av 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon ble isolert ved filtrering, vasket med vann (100 ml) og tørret. 9,3 g 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon ble derved oppnådd, mens 0,8 g 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon holdt seg oppløst i moderluten og vaskevæsker. Den totale mengde av dannet 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon var således 10,1 g (91%). The reaction mixture was then cooled to room temperature and the resulting precipitate of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone was isolated by filtration, washed with water (100 mL) and dried. 9.3 g of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone was thereby obtained, while 0.8 g of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone was kept dissolved in the mother liquor and washing liquids. The total amount of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone formed was thus 10.1 g (91%).
Eksempel 3 Example 3
Eksempel 2 ble gjentatt under anvendelse av l-fenol-4-sulfonsyre (4,4 g) istedenfor 4-hydroksy-benzoesyre. 9,6 g 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon ble oppnådd, mens 0,8 g holdt seg oppløst i moderluten og vaskevæsker. Ialt ble således 10,4 g (94%) av 4-klor-5-amino-2-fenyl-3(2H)-pyridazinon dannet. Example 2 was repeated using 1-phenol-4-sulfonic acid (4.4 g) instead of 4-hydroxy-benzoic acid. 9.6 g of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone was obtained, while 0.8 g remained dissolved in the mother liquor and washing liquids. A total of 10.4 g (94%) of 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone was thus formed.
Eksempel 4 Example 4
Eksempel 2 ble gjentatt under anvendelse av de følgende katalysatorer istedenfor 4-hydroksy-benzoesyre: (A) 3-hydroksy-2-pyridon (2,7 g), (B) 3-hydroksy-pyridin (2,4 g) og (C) 1-naftol-5-sulfonsyre (5,6 g). Example 2 was repeated using the following catalysts instead of 4-hydroxy-benzoic acid: (A) 3-hydroxy-2-pyridone (2.7 g), (B) 3-hydroxy-pyridine (2.4 g) and ( C) 1-naphthol-5-sulfonic acid (5.6 g).
Eksempel 5 Example 5
Eksempel 3 ble gjentatt idet det istedenfor et molforhold mellom utgangsmateriale og katalysator på 2:1 ble anvendt et molforhold på 10:1, svarende til 0,9 g 1-fcnyl-4-sulfonsyre istedenfor 4,4 g. Example 3 was repeated in that instead of a molar ratio between starting material and catalyst of 2:1, a molar ratio of 10:1 was used, corresponding to 0.9 g of 1-phenyl-4-sulfonic acid instead of 4.4 g.
De resulterende prøver av 4-klor-5-amino-2-f enyl-3 ( 211) - pyridazinon fra eksemplene 2, 3, 4 og 5 ble analysert (sm.p. The resulting samples of 4-chloro-5-amino-2-phenyl-3 ( 211 )-pyridazinone from Examples 2, 3, 4 and 5 were analyzed (m.p.
og G.L.C.). Resultatene er vist i tabell I. and G.L.C.). The results are shown in Table I.
Eksempel 6 Example 6
Eksempel 3 ble gjentatt under anvendelse av forskjellige molforhold mellom utgangsmateriale og katalysator. Resultatene er vist i tabell II. Example 3 was repeated using different molar ratios between starting material and catalyst. The results are shown in Table II.
Claims (4)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK461379 | 1979-10-31 | ||
| PCT/DK1980/000062 WO1981001288A1 (en) | 1979-10-31 | 1980-10-17 | Method for producing 4-chloro-5-amino-2-phenyl-3(2h)-pyridazinone from 4,5-dichloro-2-phenyl-3(2h)-pyridazinone and ammonia |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO811077L NO811077L (en) | 1981-05-14 |
| NO155578B true NO155578B (en) | 1987-01-12 |
| NO155578C NO155578C (en) | 1987-04-22 |
Family
ID=26067552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO811077A NO155578C (en) | 1979-10-31 | 1981-03-30 | PROCEDURE FOR PREPARATION OF 4-CHLORO-5-AMINO-2-PHENYL-3 (2H) -PYRIDAZINON FROM 4,5-DICHLOR-2-PHENYL-3 (2H) -PYRIDAZINON AND AMMONIA. |
Country Status (2)
| Country | Link |
|---|---|
| NO (1) | NO155578C (en) |
| SU (1) | SU1140686A3 (en) |
-
1981
- 1981-03-30 NO NO811077A patent/NO155578C/en unknown
- 1981-06-26 SU SU813304332A patent/SU1140686A3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| NO155578C (en) | 1987-04-22 |
| NO811077L (en) | 1981-05-14 |
| SU1140686A3 (en) | 1985-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101193866B (en) | Process for the synthesis of 5- (methyl-1H-imidazol-1-yl) -3- (trifluoromethyl) -benzeneamine | |
| CN105294534B (en) | Industrialized method for preparing aplidine and intermediate thereof | |
| CN113248351B (en) | Preparation method of 6-chloro-2-methoxytoluene and synthetic process of methoxyfenozide | |
| GB2198128A (en) | Dihydroxy benzene derivatives | |
| WO2011092618A1 (en) | Method for the preparation of fluazinam | |
| KR101461259B1 (en) | Process for producing toluidine compound | |
| NO155578B (en) | PROCEDURE FOR PREPARATION OF 4-CHLORO-5-AMINO-2-PHENYL-3 (2H) -PYRIDAZINON FROM 4,5-DICHLOR-2-PHENYL-3 (2H) -PYRIDAZINON AND AMMONIA. | |
| CN113277984B (en) | Method for preparing 3, 6-dichloropyridazine-4-alcohol | |
| EP0028359B1 (en) | Method for producing 4-chloro-5-amino-2-phenyl-3(2h)-pyridazinone from 4,5-dichloro-2-phenyl-3(2h)-pyridazinone and ammonia | |
| CN111116430B (en) | Preparation method of sodium taurate | |
| CN111807948B (en) | Preparation method of palladium pivalate | |
| CN109651234B (en) | Synthesis method of donepezil hydrochloride | |
| CN109678741B (en) | Preparation method of 4-amino-3-fluorobenzoic acid | |
| CN112125829A (en) | Production method of high-purity methomyl with reduced content of impurity 1, 3-dimethyl urea | |
| US6133447A (en) | Process for the preparation of substituted pyridines | |
| US2130480A (en) | Process of hydrogenating 5-nitrophthalide | |
| CN111039792B (en) | Preparation method of aniline compound | |
| CN108101836A (en) | A kind of method for preparing Cilnidipine impurity or its oxide impurity | |
| CN105801366B (en) | A kind of synthetic method of bromo alkylating agent | |
| CN112703182B (en) | Method for preparing 5-iodine-2-carboxylic acid potassium benzenesulfonate | |
| CN114249690A (en) | Synthesis method of Rosxastat | |
| JPS6125713B2 (en) | ||
| CN116410138A (en) | Synthesis method of topiramate intermediate | |
| JP4650802B2 (en) | Method for producing racemic nitrogen-containing heterocyclic derivatives | |
| WO2023189498A1 (en) | Method for producing 4,4'-dihydroxybiphenyl-3,3'-dicarboxylic acid |