CN101157635A - Method for preparing 2-nitro phenylhydrazine - Google Patents
Method for preparing 2-nitro phenylhydrazine Download PDFInfo
- Publication number
- CN101157635A CN101157635A CNA2007101354747A CN200710135474A CN101157635A CN 101157635 A CN101157635 A CN 101157635A CN A2007101354747 A CNA2007101354747 A CN A2007101354747A CN 200710135474 A CN200710135474 A CN 200710135474A CN 101157635 A CN101157635 A CN 101157635A
- Authority
- CN
- China
- Prior art keywords
- reaction
- preparation
- phenyl hydrazine
- nitro phenyl
- reduction reaction
- 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.)
- Pending
Links
- FRBUNLLUASHNDJ-UHFFFAOYSA-N (2-nitrophenyl)hydrazine Chemical compound NNC1=CC=CC=C1[N+]([O-])=O FRBUNLLUASHNDJ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 238000006722 reduction reaction Methods 0.000 claims abstract description 8
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims abstract description 5
- 235000010262 sodium metabisulphite Nutrition 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- 238000006193 diazotization reaction Methods 0.000 claims abstract description 4
- 230000007062 hydrolysis Effects 0.000 claims abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 230000002829 reductive effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 abstract 1
- 229940001584 sodium metabisulfite Drugs 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000010009 beating Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of 2-nitro phenyl hydrazine. By using 2-nitroaniline as the initial raw material, the preparation method is capable of producing the 2-nitro phenyl hydrazine after the diazotization reaction, the reduction reaction and hydrolysis, wherein, the reduction reaction which utilizes sodium metabisulfite as the reduction agent is carried out under the conditions that the temperature is 10 and 35 DEG C and the PH value is 7 to 9. The 2-nitro phenyl hydrazine produced by the preparative method of the invention has the advantages of high product purity and low production cost.
Description
Technical field
The present invention relates to a kind of preparation method of 2-nitrophenyl hydrazine.
Background technology
The 2-nitrophenyl hydrazine is a kind of important intermediate, especially a kind of medicine intermediate, prior art is a raw material with the 2-N-methyl-p-nitroaniline, through diazotization reaction, S-WAT reduction, hydrolysis, the synthetic method of the 2-nitrophenyl hydrazine for preparing, long reaction time generally needs yield only to be 63-72%, and the production cost height.
Summary of the invention
Technical problem to be solved by this invention provides a kind of preparation method of 2-nitrophenyl hydrazine, the 2-nitrophenyl hydrazine product purity height that obtains by this method, and production cost is low.
For solving above technical problem, the present invention adopts following technical scheme:
A kind of preparation method of 2-nitrophenyl hydrazine is a starting raw material with the 2-N-methyl-p-nitroaniline, through diazotization reaction, reduction reaction, hydrolysis prepares the 2-nitrophenyl hydrazine, described reduction reaction is reductive agent with the Sodium Pyrosulfite, and at 10-35 ℃, pH carries out under the condition of 7-9.
Because the technique scheme utilization, the present invention compared with prior art has following advantage:
Adopt Sodium Pyrosulfite as reductive agent, shortened the reaction times greatly, generally only need half hour can reach reaction end, production cost is low, and the product purity height (greater than 98%) that makes.
Embodiment
Below the specific embodiment of the present invention is described:
In the 500ml beaker, add entry 2510ml, 10N hydrochloric acid 50ml stirs, and adds levigated 2-N-methyl-p-nitroaniline 27.6 grams, fully making beating was cooled to solution below 5 ℃ after 30 minutes, slowly add sodium nitrite solution (being made into by 15 gram Sodium Nitrites and 30ml water) then, finish, regulation system pH is 1-2, control temperature 8-10 ℃ of reaction system, stirring reaction 1.5-2 hour, stopped reaction filtered and reservation filtrate.
In the 1000ml beaker, add entry 250ml, stir and to add Sodium Pyrosulfite 100 grams down, treat that its dissolving back adds sodium hydroxide 130 grams, cooling solution to 12 ℃, slowly add above-mentioned filtrate then, controlled temperature 12-15 ℃, pH is 7, reacts to add 115 gram hydrochloric acid after 30 minutes, heat to 70 ℃, react after 2 hours, cooling solution to 20 ℃, filter filter cake.
Add hydrochloric acid 300 gram in the 500ml beaker, stir and add filter cake, pulled an oar 30 minutes, heat to 80-90 ℃, insulation reaction 2 hours is cooled to 20 ℃, filter product.HPLC＝98.05％。
Claims (1)
1. the preparation method of a 2-nitrophenyl hydrazine is a starting raw material with the 2-N-methyl-p-nitroaniline, through diazotization reaction, reduction reaction, hydrolysis prepares the 2-nitrophenyl hydrazine, it is characterized in that: described reduction reaction is reductive agent with the Sodium Pyrosulfite, and at 10-35 ℃, pH carries out under the condition of 7-9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007101354747A CN101157635A (en) | 2007-11-12 | 2007-11-12 | Method for preparing 2-nitro phenylhydrazine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007101354747A CN101157635A (en) | 2007-11-12 | 2007-11-12 | Method for preparing 2-nitro phenylhydrazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101157635A true CN101157635A (en) | 2008-04-09 |
Family
ID=39305885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007101354747A Pending CN101157635A (en) | 2007-11-12 | 2007-11-12 | Method for preparing 2-nitro phenylhydrazine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101157635A (en) |
-
2007
- 2007-11-12 CN CNA2007101354747A patent/CN101157635A/en active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Open date: 20080409 |