CN104803920A - 3,6-dibromopyridazide synthesis method - Google Patents
3,6-dibromopyridazide synthesis method Download PDFInfo
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- CN104803920A CN104803920A CN201510146392.7A CN201510146392A CN104803920A CN 104803920 A CN104803920 A CN 104803920A CN 201510146392 A CN201510146392 A CN 201510146392A CN 104803920 A CN104803920 A CN 104803920A
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- pyridazine
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- dibromo
- synthetic method
- dihydroxy
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- VQAFMTSSCUETHA-UHFFFAOYSA-N 3,6-dibromopyridazine Chemical compound BrC1=CC=C(Br)N=N1 VQAFMTSSCUETHA-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000001308 synthesis method Methods 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 58
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 238000000746 purification Methods 0.000 claims abstract description 3
- 238000010189 synthetic method Methods 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical compound [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 claims description 14
- 238000010898 silica gel chromatography Methods 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- AQZJVJXVTVCMCZ-UHFFFAOYSA-N 3,4-dibromopyridazine Chemical compound BrC1=CC=NN=C1Br AQZJVJXVTVCMCZ-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- 238000001035 drying Methods 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 5
- GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- VHVUTJZQFZBIRR-UHFFFAOYSA-N 1h-pyridazin-4-one Chemical compound OC1=CC=NN=C1 VHVUTJZQFZBIRR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UZRZWRDICWBWBA-UHFFFAOYSA-N 3,6-dichloro-1h-pyridazin-4-one Chemical compound ClC1=CC(=O)C(Cl)=NN1 UZRZWRDICWBWBA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000001291 vacuum drying 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
- C07D237/12—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention belongs to the field of organic synthesis, and particularly relates to a 3,6-dibromopyridazide synthesis method which comprises the following steps: using 3,6-dihydroxypyridazine and phosphorus oxybromide as raw materials for a reaction in an appropriate solvent at 0-120 DEG C; carrying out purification to obtain a pure product of 3,6-dibromopyridazide. The reaction raw materials are relatively easy to obtain and reasonable in price; the 3,6-dibromopyridazide synthesis method is mild in reaction condition, easy to operate and control, simple in post-treatment, stable in product quality and high in product purity.
Description
(1) technical field
The invention belongs to organic synthesis field, be specifically related to a kind of synthetic method of 3,6-dibromo pyridazine.
(2) background technology
3,6-dibromo pyridazine is the important intermediate of organic synthesis, is mainly used in medicine intermediate, organic synthesis, organic solvent, also can be applicable to the aspects such as DYE PRODUCTION, pesticide producing and spices.This medicine intermediate is more novel, has very large using value.But lack the literature record of relevant 3,6-dibromo pyridazine.
On December 3rd, 2012, having declared with 3,6-dichloro-pyridazine is that raw material prepares 4-bromine pyridazine through four-step reaction, and concrete preparation method is as follows:
(1), get 3,6-dichloro-pyridazine and put into container, under stirring, be warmed up to 80 ~ 160 DEG C, make 3,6-dichloro-pyridazine all dissolves, and then in 3,6-dichloro-pyridazine solution, passes into chlorine, control temperature is 80 ~ 160 DEG C and carries out reaction 4 ~ 10h, after reaction terminates, reaction solution is poured in sherwood oil, and at room temperature crystallization, suction filtration, obtain 3 after drying, 4,6-trichlorine pyridazine white powder;
(2), according to 3,4, the mol ratio of 6-trichlorine pyridazine and NaOH is 1:1 ~ 5, getting in step () 3,4,6-obtained trichlorine pyridazine white powders, to join concentration be in the NaOH solution of 5 ~ 15%, reflux after heating for dissolving 4 ~ 10h at 100 DEG C, reaction solution adds HCL and adjusts pH value to be 1.0, standing post crystallization, suction filtration, again with dehydrated alcohol recrystallization, obtain 3,6-bis-chloro-4-hydroxypyridazin pale yellow powder through vacuum-drying again;
(3), by obtained for step (two) 3,6-bis-chloro-4-hydroxypyridazin powder adds in autoclave, first add anhydrous methanol fully to dissolve, then sodium hydroxide and palladium carbon catalyst is added, sealed reactor, pass into the air in hydrogen exchange reactor, then continuing to pass into hydrogen makes the pressure in reactor remain on 1.0 ~ 2.0MPa, controlling temperature of reaction is 20 ~ 80 DEG C, reaction 4 ~ 10h, reactant carries out suction filtration, by filtrate reduced in volume, use dehydrated alcohol recrystallization, drying again, obtain 4-hydroxypyridazin pale yellow powder;
In described step (three), 3, the 6-bis-chloro-4-amino pyridazine of every 1kg add 100-400g sodium hydroxide and 10-50g
Palladium carbon catalyst;
The palladium carbon catalyst of described palladium carbon catalyst to be palladium content be 5% or 10%;
(4), be 1:1 ~ 5 according to the mol ratio of 4-hydroxypyridazin and tribromo oxygen phosphorus, getting 4-hydroxypyridazin obtained in step (three) adds in tribromo oxygen phosphorus, controlling temperature of reaction is 60 ~ 120 DEG C, reaction 0.5 ~ 5h, reaction solution 60 DEG C is evaporated to dry, slow dropping frozen water, until by the thorough cancellation of tribromo oxygen phosphorus, then the strong aqua that concentration is 25% is added, solution ph is adjusted to 8.0, extract with chloroform again, get organic phase anhydrous magnesium sulfate and carry out drying, suction filtration is carried out after drying, get filtrate and put into rotatory evaporator, decompression steams chloroform, then silica gel column chromatography is carried out, use petroleum ether solvent wash-out, collect effluent liquid and carry out underpressure distillation, use hexanaphthene recrystallization again, dry, obtain 4-bromine pyridazine yellow powder.
Reactions steps is loaded down with trivial details, and raw material is not easy to obtain, and needs to improve.
(3) summary of the invention
The present invention, in order to make up the deficiencies in the prior art, provides the synthetic method of 3,6-dibromo pyridazine, and this synthetic method is simple to operate, productive rate is high, is applicable to laboratory and suitability for industrialized production.
The present invention is achieved through the following technical solutions:
A kind of synthetic method of 3,6-dibromo pyridazine, its special character is: comprise the following steps:
With 3,6-dihydroxy pyridazine and tribromo oxygen phosphorus for raw material, in suitable solvent, in 0-120 DEG C of reaction, after purifying sterling 3,6-dibromo pyridazine.
The synthetic method of 3,6-dibromo pyridazines of the present invention, in described step, reactant is 3,6-dihydroxy pyridazine and tribromo oxygen phosphorus, and charging capacity is 3,6-dihydroxy pyridazine: tribromo oxygen phosphorus=1:0.8-3, is more than mol ratio.
The synthetic method of 3,6-dibromo pyridazines of the present invention, described solvent is one or both in methylene dichloride, chloroform, ethanol, benzene, DMF, toluene and water.
The synthetic method of 3,6-dibromo pyridazines of the present invention, in described step, purification step is evaporation concentration, recrystallization, and silica gel column chromatography is separated.
The synthetic method of 3,6-dibromo pyridazines of the present invention, the charging capacity of reactant and solvent is: 3,6-dihydroxy pyridazine: solvent=1:1-10, is more than weight ratio.
The synthetic method of 3,6-dibromo pyridazines of the present invention, in described step, the reaction times is 1-30 hour.
Beneficial effect of the present invention: reaction raw materials compares and is easy to get, reasonable price, reaction conditions is gentle, easy handling, is easy to control, and aftertreatment is simple, and constant product quality, purity is high.
(4) embodiment
Embodiment 1:
3,6-dihydroxy pyridazine (1.10g, 10mmol) is added, tribromo oxygen phosphorus (5.73g, 20mmol), chloroform 8ml in 50mL single necked round bottom flask.Mixture in reaction flask stirring reaction 4 hours at 90 DEG C.TLC and GC determines that reaction completes.After reaction terminates, revolve and steam except desolventizing, obtain thick product, be separated with silica gel column chromatography and obtain straight product 3,6-dibromo pyridazine, after drying, calculated yield 42.60%, purity 98.50% (GC), fusing point 118.5 DEG C-119.2 DEG C (117 DEG C-121 DEG C, document).Nuclear magnetic resonance spectroscopy: 1H NMR (deuterochloroform): 7.529 ppm (s, 1H).
Embodiment 2:
3,6-dihydroxy pyridazine (1.10g, 10mmol) is added, tribromo oxygen phosphorus (6.88g, 24mmol), methylene dichloride 8ml in 50mL single necked round bottom flask.Mixture in reaction flask stirring reaction 4 hours at 90 DEG C.TLC and GC determines that reaction completes.After reaction terminates, revolve and steam except desolventizing, obtain thick product, be separated with silica gel column chromatography and obtain straight product 3,6-dibromo pyridazine, after drying, calculated yield 45.21%, purity 99.02% (GC), fusing point 118.5 DEG C-119.2 DEG C (117 DEG C-121 DEG C, document).
Embodiment 3:
3,6-dihydroxy pyridazine (5.60g, 50mmol) is added, tribromo oxygen phosphorus (28.67g, 100mmol), DMF 50ml in 250mL single necked round bottom flask.Mixture in reaction flask stirring reaction 4 hours at 90 DEG C.TLC and GC determines that reaction completes.After reaction terminates, revolve and steam except desolventizing, obtain thick product, be separated with silica gel column chromatography and obtain straight product 3,6-dibromo pyridazine, after drying, calculated yield 43%.
Embodiment 4:
3,6-dihydroxy pyridazine (11.20g, 100mmol) is added, tribromo oxygen phosphorus (86.00g, 300mmol), ethanol 100ml in 500mL single necked round bottom flask.Mixture in reaction flask stirring reaction 4 hours at 90 DEG C.TLC and GC determines that reaction completes.After reaction terminates, revolve and steam except desolventizing, obtain thick product, be separated with silica gel column chromatography and obtain straight product 3,6-dibromo pyridazine, after drying, calculated yield 47.25%.
Embodiment 5:
3,6-dihydroxy pyridazine (11.20g, 100mmol) is added, phosphorus oxychloride (57.34g, 200mmol), chloroform and DMF 110ml altogether in 500mL single necked round bottom flask.Mixture in reaction flask stirring reaction 4 hours at 90 DEG C.TLC and GC determines that reaction completes.After reaction terminates, revolve and steam except desolventizing, obtain thick product, be separated with silica gel column chromatography and obtain straight product 3,6-dibromo pyridazine, after drying, calculated yield 45.28%.
Embodiment 6:
3,6-dihydroxy pyridazine (11.20g, 100mmol) is added, phosphorus oxychloride (22.94g, 80mmol), benzene 100ml in 500mL single necked round bottom flask.Mixture in reaction flask stirring reaction 15 hours at 120 DEG C.TLC and GC determines that reaction completes.After reaction terminates, revolve and steam except desolventizing, obtain thick product, be separated with silica gel column chromatography and obtain straight product 3,6-dibromo pyridazine, after drying, calculated yield 45.96%.
Embodiment 7:
3,6-dihydroxy pyridazine (11.20g, 100mmol) is added, phosphorus oxychloride (22.94g, 80mmol), benzene 80ml, water 30ml in 500mL single necked round bottom flask.Mixture in reaction flask stirring reaction 30 hours at 0 DEG C.TLC and GC determines that reaction completes.After reaction terminates, revolve and steam except desolventizing, obtain thick product, be separated with silica gel column chromatography and obtain straight product 3,6-dibromo pyridazine, after drying, calculated yield 45.45%.
Embodiment 8:
3,6-dihydroxy pyridazine (11.20g, 100mmol) is added, phosphorus oxychloride (22.94g, 80mmol), benzene 80ml, water 30ml in 500mL single necked round bottom flask.Mixture in reaction flask stirring reaction 1 hour at 70 DEG C.TLC and GC determines that reaction completes.After reaction terminates, revolve and steam except desolventizing, obtain thick product, be separated with silica gel column chromatography and obtain straight product 3,6-dibromo pyridazine, after drying, calculated yield 45.45%.
Embodiment 9:
3,6-dihydroxy pyridazine (1.10g, 10mmol) is added, tribromo oxygen phosphorus (6.88g, 24mmol), methylene dichloride 1ml in 50mL single necked round bottom flask.Mixture in reaction flask stirring reaction 4 hours at 30 DEG C.TLC and GC determines that reaction completes.After reaction terminates, revolve and steam except desolventizing, obtain thick product, be separated with silica gel column chromatography and obtain straight product 3,6-dibromo pyridazine, after drying, calculated yield 45.51%, purity 99.02% (GC), fusing point 118.5 DEG C-119.2 DEG C (117 DEG C-121 DEG C, document).
Embodiment 10:
3,6-dihydroxy pyridazine (22.4g, 200mmol) is added, phosphorus oxychloride (22.94g, 80mmol), DMF50ml, water 60ml in 500mL single necked round bottom flask.Mixture in reaction flask stirring reaction 0.4 hour at 100 DEG C.TLC and GC determines that reaction completes.After reaction terminates, revolve and steam except desolventizing, obtain thick product, be separated with silica gel column chromatography and obtain straight product 3,6-dibromo pyridazine, after drying, calculated yield 90.1%.
Claims (6)
1. the synthetic method of a dibromo pyridazine, is characterized in that: comprise the following steps:
With 3,6-dihydroxy pyridazine and tribromo oxygen phosphorus for raw material, in suitable solvent, in 0-120 DEG C of reaction, after purifying sterling 3,6-dibromo pyridazine.
2. the synthetic method of 3,6-dibromo pyridazines according to claim 1, is characterized in that: in described step, and reactant is 3,6-dihydroxy pyridazine and tribromo oxygen phosphorus, and charging capacity is 3,6-dihydroxy pyridazine: tribromo oxygen phosphorus=1:0.8-3, is more than mol ratio.
3. the synthetic method of 3,6-dibromo pyridazines according to claim 1 and 2, is characterized in that: described solvent is one or both in methylene dichloride, chloroform, ethanol, benzene, DMF, toluene and water.
4. the synthetic method of 3,6-dibromo pyridazines according to claim 1 and 2, is characterized in that: in described step, purification step is evaporation concentration, recrystallization, and silica gel column chromatography is separated.
5. the synthetic method of 3,6-dibromo pyridazines according to claim 1 and 2, it is characterized in that: the charging capacity of reactant and solvent is: 3,6-dihydroxy pyridazine: solvent=1:1-10, is more than weight ratio.
6. the synthetic method of 3,6-dibromo pyridazines according to claim 1 and 2, is characterized in that: in described step, the reaction times is 1-30 hour.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110903248A (en) * | 2019-12-25 | 2020-03-24 | 郑州华赞医药科技有限公司 | Synthesis method of 5-chloro-4-aminopyridazine |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN86104837A (en) * | 1985-06-14 | 1986-12-31 | 伊莱利利公司 | Fungicidal pyrisazines |
| CN102924386A (en) * | 2012-12-03 | 2013-02-13 | 洛阳师范学院 | Industrial preparation method of 4-bromopyridazine |
| CN104447569A (en) * | 2014-11-05 | 2015-03-25 | 定陶县友帮化工有限公司 | Method for synthetizing 3,6-dichloropyridazine |
-
2015
- 2015-03-31 CN CN201510146392.7A patent/CN104803920A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN86104837A (en) * | 1985-06-14 | 1986-12-31 | 伊莱利利公司 | Fungicidal pyrisazines |
| CN102924386A (en) * | 2012-12-03 | 2013-02-13 | 洛阳师范学院 | Industrial preparation method of 4-bromopyridazine |
| CN104447569A (en) * | 2014-11-05 | 2015-03-25 | 定陶县友帮化工有限公司 | Method for synthetizing 3,6-dichloropyridazine |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110903248A (en) * | 2019-12-25 | 2020-03-24 | 郑州华赞医药科技有限公司 | Synthesis method of 5-chloro-4-aminopyridazine |
| CN110903248B (en) * | 2019-12-25 | 2023-04-07 | 郑州华赞医药科技有限公司 | Synthesis method of 5-chloro-4-aminopyridazine |
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