AU2018100365A4 - Antagonists medicine intermediates o-nitrobenzoic acid synthesis method - Google Patents
Antagonists medicine intermediates o-nitrobenzoic acid synthesis method Download PDFInfo
- Publication number
- AU2018100365A4 AU2018100365A4 AU2018100365A AU2018100365A AU2018100365A4 AU 2018100365 A4 AU2018100365 A4 AU 2018100365A4 AU 2018100365 A AU2018100365 A AU 2018100365A AU 2018100365 A AU2018100365 A AU 2018100365A AU 2018100365 A4 AU2018100365 A4 AU 2018100365A4
- Authority
- AU
- Australia
- Prior art keywords
- solution
- nitrobenzoic acid
- mol
- mass fraction
- synthesis method
- 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.)
- Ceased
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Abstract Antagonists medicine intermediates o-nitrobenzoic acid synthesis method, comprises the following steps: the reaction vessel were added 3 mol 5 2-ethyl-3-nitrophenol, 4-5 mol of ethylene glycol monopropyl ether solution, raised the temperature of the solution to 30-35 *C, controlled the stirring speed at 150-170 rpm, kept for 30-50 min, then added 6-7 mol triphenylphosphine powder, continued to reacted for 60-90 min, reduced the temperature of the solution to 5-8 0C, after the solid precipitated, filtrated, washed with propionic anhydride solution, washed with 10 triethylamine solution, recrystallizated in a 2-methylpentane solution and dehydrated with the dehydrating agent, got o-nitrobenzoic acid crystals.
Description
FIELD OF THE INVENTION
The present invention relates to antagonists medicine intermediates o-nitrobenzoic 5 acid synthesis method.
GENERAL BACKGROUND
O-nitrobenzoic acid is mainly used for pharmaceutical synthesis and organic synthesis, it can also be used for 5HT2-D2 antagonist drug intermediates synthesis.
However, most of the existing synthetic methods are using potassium permanganate as a reactant, it is complicated and the final yield is not very high. Therefore, it is necessary to propose a new synthetic method for further improving the quality and yield of the product and reducing the byproduct content, it has important economic significance.
SUMMARY
The purpose of the present invention is to provide antagonists medicine intermediates o-nitrobenzoic acid synthesis method, comprises the following steps:
(i) the reaction vessel were added 3 mol 2-ethyl-3-nitrophenol, 4-5 mol of ethylene glycol monopropyl ether solution, raised the temperature of the solution to 30-35 °C, controlled the stirring speed at 150-170 rpm, kept for 30-50 min, then added 6-7 mol triphenylphosphine powder, continued to reacted for 60-90 min, reduced the temperature of the solution to 5-8 °C, after the solid precipitated, filtrated, washed with propionic anhydride solution, washed with triethylamine solution, recrystallizated in a
2-methylpentane solution and dehydrated with the dehydrating agent, got o-nitrobenzoic acid crystals; wherein, the ethylene glycol monopropyl ether solution in step (i) has a mass fraction of 75-80%, the mass fraction of the propionic anhydride solution in step (i) is 85 to 90%, the mass fraction of the triethylamine solution in step (i) is 91 to 94%, the 2-methylpentane solution described in step (i) has a mass fraction is
90-95%.
2018100365 25 Mar 2018
Throughout the reaction process can be the following reaction formula:
Advantage of the present invention is that: reducing intermediate links reaction, decreasing the reaction time and improving the reaction yield.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The following examples with reference to specific embodiments of the present invention are further illustrated:
antagonists medicine intermediates o-nitrobenzoic acid synthesis method.
Embodiment 1
The reaction vessel were added 3 mol 2-ethyl-3-nitrophenol and 4 mol ethylene glycol monopropyl ether with a mass fraction of 75%, the temperature ofthe solution was raised to 30 °C and the stirring speed was controlled at 150 rpm for 30min, then added 6 mol triphenylphosphine powder, continued to react for 60 min, reduced the temperature of the solution to 5 °C, precipitated the solid, filtered, washed with propionic anhydride solution with a mass fraction of 85%, and washed with amine solution with a mass fraction of 91%, and then recrystallized in 2-methyl pentane solution with a mass fraction of 90%, dehydrated with agent dehydration, got crystal o-nitrobenzoic acid 445.89g, yield 89%.
Embodiment 2
The reaction vessel were added 3 mol 2-ethyl-3-nitrophenol and 4.5 mol ethylene 25 glycol monopropyl ether with a mass fraction of 78%, the temperature ofthe solution was raised to 32 °C and the stirring speed was controlled at 160 rpm for 40min, then added 6.5 mol triphenylphosphine powder, continued to react for 70 min, reduced the
2018100365 25 Mar 2018 temperature of the solution to 6 °C, precipitated the solid, fdtered, washed with propionic anhydride solution with a mass fraction of 88%, and washed with amine solution with a mass fraction of 92%, and then recrystallized in 2-methyl pentane solution with a mass fraction of 93%, dehydrated with agent dehydration, got crystal o-nitrobenzoic acid 460.92g, yield 92%.
Embodiment 3
The reaction vessel were added 3 mol 2-ethyl-3-nitrophenol and 5 mol ethylene glycol monopropyl ether with a mass fraction of 80%, the temperature of the solution was raised to 35 °C and the stirring speed was controlled at 170 rpm for 50min, then added 7 mol triphenylphosphine powder, continued to react for 90 min, reduced the temperature of the solution to 8 °C, precipitated the solid, filtered, washed with propionic anhydride solution with a mass fraction of 90%, and washed with amine solution with a mass fraction of 94%, and then recrystallized in 2-methyl pentane solution with a mass fraction of 95%, dehydrated with agent dehydration, got crystal o-nitrobenzoic acid 475.95g, yield 95%.
2018100365 25 Mar 2018
Claims (3)
- Claims1. Antagonists medicine intermediates o-nitrobenzoic acid synthesis method, comprises the following steps:(i) the reaction vessel were added 3 mol
- 2-ethy 1-3-nitrophenol, 4-5 mol of 5 ethylene glycol monopropyl ether solution, raised the temperature of the solution to 30-35 °C, controlled the stirring speed at 150-170 rpm, kept for 30-50 min, then added 6-7 mol triphenylphosphine powder, continued to reacted for 60-90 min, reduced the temperature of the solution to 5-8 °C, after the solid precipitated, filtrated, washed with propionic anhydride solution, washed with triethylamine solution,10 recrystallizated in a 2-methylpentane solution and dehydrated with the dehydrating agent, got o-nitrobenzoic acid crystals; wherein, the ethylene glycol monopropyl ether solution in step (i) has a mass fraction of 75-80%, the mass fraction of the propionic anhydride solution in step (i) is 85 to 90%.15 2. Antagonists medicine intermediates o-nitrobenzoic acid synthesis method according to claim 1 wherein the mass fraction of the triethylamine solution in step (i) is 91 to 94%.
- 3. Antagonists medicine intermediates o-nitrobenzoic acid synthesis method20 according to claim 1 wherein the 2-methylpentane solution described in step (i) has a mass fraction is 90-95%.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710185280.1A CN108623464A (en) | 2017-03-26 | 2017-03-26 | A kind of synthetic method of antagonist pharmaceuticals intermediate o-nitrobenzoic acid |
| CN2017101852801 | 2017-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2018100365A4 true AU2018100365A4 (en) | 2018-05-10 |
Family
ID=58682504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2018100365A Ceased AU2018100365A4 (en) | 2017-03-26 | 2018-03-25 | Antagonists medicine intermediates o-nitrobenzoic acid synthesis method |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN108623464A (en) |
| AU (1) | AU2018100365A4 (en) |
| GB (1) | GB201705516D0 (en) |
-
2017
- 2017-03-26 CN CN201710185280.1A patent/CN108623464A/en active Pending
- 2017-04-05 GB GBGB1705516.1A patent/GB201705516D0/en not_active Ceased
-
2018
- 2018-03-25 AU AU2018100365A patent/AU2018100365A4/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CN108623464A (en) | 2018-10-09 |
| GB201705516D0 (en) | 2017-05-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2018100365A4 (en) | Antagonists medicine intermediates o-nitrobenzoic acid synthesis method | |
| CN108892627B (en) | Process for synthesizing taurine by one-pot method | |
| CN108623488B (en) | Synthetic method of aminomethylbenzoic acid | |
| IES86986B2 (en) | Antagonists medicine intermediates o-nitrobenzoic acid synthesis method | |
| JP6028606B2 (en) | Method for producing amine compound | |
| CN105061375B (en) | Method for preparing 3-isochromanone | |
| AU2018100389A4 (en) | Drugs intermediates m-aminobenzoic acid synthesis method | |
| AU2018100422A4 (en) | Drugs intermediates 2-ethylhexanoic acid synthesis method | |
| AU2018100387A4 (en) | Organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method | |
| CN104387325B (en) | The synthetic method of the imidazolidinone of 1 chloroformyl, 3 mesyl 2 | |
| AU2018100415A4 (en) | Drugs intermediates 1,4-dibromo-2,3-butanediol synthesis method | |
| IES86996B2 (en) | Organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method | |
| AU2018100388A4 (en) | Medicine intermediates sulfanilic acid synthesis method | |
| AU2018100367A4 (en) | Fluconazole drugs intermediates 2,4-dinitrobenzoic acid synthesis method | |
| AU2018100364A4 (en) | Rivanol medicine intermediates 2-chloro-4-nitrobenzoic acid synthesis method | |
| CN103772333A (en) | Method for synthesizing cis-4-cyclohexene-1, 2-dimethylbenzene anhydride | |
| CN117050011B (en) | Method for synthesizing 2-methylquinoline by using vinyl acetate as raw material | |
| AU2018100395A4 (en) | Drug intermediates parachlorobenzoic-acid synthesis method | |
| CN102408374A (en) | Synthesis method of 1-(methylsulphonyl)imidazolidin-2-one | |
| CN108117490B (en) | Preparation method of p-nitrobenzyl alcohol | |
| AU2018100391A4 (en) | Organic synthesis intermediates 2-aminobenzothiazole synthesis method | |
| AU2018100399A4 (en) | Polyester fiber dyeing modifier isophthalic acid synthesis method | |
| US2803649A (en) | 1, 2-dihalogenopropiono-hydroxamic acid and process for producing same | |
| CN106632001A (en) | Preparation method of 4-(bromoacetyl) pyridine hydrobromide | |
| AU2018100362A4 (en) | Organic synthesis intermediates N-propenyl urea synthesis method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGI | Letters patent sealed or granted (innovation patent) | ||
| MK22 | Patent ceased section 143a(d), or expired - non payment of renewal fee or expiry |