JPS61233656A - 2-fluoro-5-nitrophenylhydrazine and production thereof - Google Patents
2-fluoro-5-nitrophenylhydrazine and production thereofInfo
- Publication number
- JPS61233656A JPS61233656A JP7385385A JP7385385A JPS61233656A JP S61233656 A JPS61233656 A JP S61233656A JP 7385385 A JP7385385 A JP 7385385A JP 7385385 A JP7385385 A JP 7385385A JP S61233656 A JPS61233656 A JP S61233656A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- expressed
- fluoro
- nitrophenylhydrazine
- 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.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は構造式（１）
テ表ワされる２−フルオロ−５−二トロフェニルヒドラ
ジン及びその製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to 2-fluoro-5-nitrophenylhydrazine represented by structural formula (1) and a method for producing the same.
本発明の２−フルオロ−５−二トロフェニルヒドラジン
は文献未記載の新規化合物であり、除草剤の有用な中間
体、例えば特開昭５９−８４８７２号公報及び特開昭５
９−１７００７１号公報等に記載の除草剤の中間体とな
１．つる化合物である。The 2-fluoro-5-nitrophenylhydrazine of the present invention is a new compound that has not been described in any literature, and is a useful intermediate for herbicides, such as those disclosed in JP-A-59-84872 and JP-A-Sho 5.
9-170071, etc. as intermediates for herbicides 1. It is a vine compound.
本発明の構造式（１）で表わされる２−フルオロ−５−
ニトロフェニルヒドラジンの製造方法を図示すると下記
の通りとなる。2-fluoro-5- represented by structural formula (1) of the present invention
The method for producing nitrophenylhydrazine is illustrated below.
即ち構造式（ＩＩ）で表わされるアニリン誘導体を塩酸
で処理し、該アニリン誘導体の塩酸塩としだ後亜硝酸ソ
ーダと反応させて構造式（■′）で表わされるジアゾニ
ウム塩とし、該ジアゾニウム塩を単離することなく還元
剤により還元することにより構造式（１）で表わされる
２−フルオロ−５−＝ トｏフェニルヒドラジンを得る
ことができる。That is, the aniline derivative represented by the structural formula (II) is treated with hydrochloric acid to form the hydrochloride salt of the aniline derivative, and then reacted with sodium nitrite to form the diazonium salt represented by the structural formula (■'). 2-fluoro-5-tophenylhydrazine represented by structural formula (1) can be obtained by reduction with a reducing agent without isolation.
本反応に使用できる溶媒としては本反応の進行を阻害し
ないものであれば良く、通常は水を溶媒として行なわれ
るが、構造式（Ｉｆ）で表わされるアニリン誘導体の塩
酸塩を製造する際に塩の生成を容易に行う目的で、構造
式（Ｔｌ）で表わされるアニリン誘導体を溶解し且つ以
後の反応の進行を阻害しない溶媒を用いることができ、
例えば酢酸等を挙げることができる。The solvent that can be used in this reaction is any solvent as long as it does not inhibit the progress of this reaction, and water is usually used as a solvent. For the purpose of facilitating the production of, a solvent can be used that dissolves the aniline derivative represented by the structural formula (Tl) and does not inhibit the progress of the subsequent reaction,
For example, acetic acid can be mentioned.
本反応で使用することができる還元剤としては、例えば
亜硫酸ナトリウム、亜硫酸ガス、ナトリウムハイドロサ
ルファイド、塩化第一スズ等を挙げることができるが、
本発明はこれらに限定されるものではない。Examples of reducing agents that can be used in this reaction include sodium sulfite, sulfur dioxide gas, sodium hydrosulfide, stannous chloride, etc.
The present invention is not limited to these.
構造式（ＩＩ）で表わされるアニリン誘導体を塩酸及び
亜硝酸ソーダでジアゾ化し、次いで還元剤で処理して目
的とする構造式（１）で表わされるヒドラジンを製造す
る際反応試剤の割合は、構造式（ＩＩ）で表わされるア
ニリン誘導体１モルに対して、塩酸にあっては過剰に使
用すれば良く、亜硝酸ソーダにあっては等モル量乃至過
剰に使用すれば良く、又還元剤は使用する還元剤の種類
によって一定しないが目的とする構造式（Ｉ）で表わさ
れるヒドラジンが充分生成する量を使用すれば良い。When the aniline derivative represented by the structural formula (II) is diazotized with hydrochloric acid and sodium nitrite, and then treated with a reducing agent to produce the desired hydrazine represented by the structural formula (1), the proportion of the reaction reagent is determined according to the structure. For 1 mole of the aniline derivative represented by formula (II), hydrochloric acid may be used in excess, sodium nitrite may be used in an equimolar amount or in excess, and reducing agents may be used. Although the amount varies depending on the type of reducing agent used, it is sufficient to use an amount sufficient to produce the desired hydrazine represented by structural formula (I).
本反応は一般的には冷却下、例えば−２０℃乃至１０℃
の範囲から適宜選択することができる。This reaction is generally carried out under cooling, e.g. -20°C to 10°C.
It can be selected as appropriate from the range.
反応時間は０．５乃至４８時間の範囲から適宜選択すれ
ば良い。The reaction time may be appropriately selected from the range of 0.5 to 48 hours.
反応終了後適当な溶媒で目的物を抽出し濾過単離すれば
良く、得られた目的物はそのまま次の反応に使用するこ
ともでき又必要に応じて精製処理を行い次の反応に供し
ても良い・。After the completion of the reaction, the target product can be extracted with an appropriate solvent and isolated by filtration, and the obtained target product can be used as it is in the next reaction, or if necessary, it can be purified and used in the next reaction. Good too.
以下に本発明の実施例を示すが本発明はこれらに限定さ
れるものではない。Examples of the present invention are shown below, but the present invention is not limited thereto.
実施例１
２−フルオロ−５−ニトロアニリン３．１２ｙ（α０２
モル）を酢酸５ ｍｌに溶解した後塩酸１０ｄを加えた
。この溶液Ａに、水４ ｆｉｌに溶解した亜硫酸ナトリ
ウム１．５２ｙ（（ＬＯ’２２モル）の溶液Ｂを一２℃
で滴下した。滴下終了後この溶液を、塩化第一スズ１！
Ｌ５４Ｆを１５ｍ７の塩酸に溶解した溶液Ｃに一１０℃
〜−５℃で２０分かけて滴下した後冷却下１時間攪拌を
行った。反応終了後析出物を炉果し、この析出物に水を
加え水酸化ナトリウム水溶液で塩基性とし、エーテルで
抽出し抽出液を乾燥した後溶媒を留去することによす目
的物である２−フルオロ−５−二トロフェニルヒドラジ
ン１．６Ｂｙを結晶物として得る。Example 1 2-fluoro-5-nitroaniline 3.12y (α02
After dissolving mol) in 5 ml of acetic acid, 10 d of hydrochloric acid was added. To this solution A, add solution B of 1.52y ((LO'22 mol) of sodium sulfite dissolved in 4 fil of water at -2℃).
It was dripped. After completing the dropping, add 1 ml of this solution to stannous chloride.
Add solution C prepared by dissolving L54F in 15m7 of hydrochloric acid to -10°C.
The mixture was added dropwise at ~-5°C over 20 minutes, and then stirred for 1 hour while cooling. After the reaction is complete, the precipitate is dried in the oven, water is added to the precipitate, made basic with an aqueous sodium hydroxide solution, extracted with ether, the extract is dried, and the solvent is distilled off to obtain the desired product. 1.6 By of -fluoro-5-nitrophenylhydrazine is obtained as a crystalline product.
収率４９１チ ＮＭＲスペクトルデータ 、ＴＭＳYield: 491 cm NMR spectrum data , TMS
Claims (2)
ジン。(1) Structural formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼2-Fluoro-5-nitrophenylhydrazine represented by (I).
することを特徴とする構造式（ I ）▲数式、化学式、
表等があります▼（ I ） で表わされる２−フルオロ−５−ニトロフェニルヒドラ
ジンの製造方法。(2) Structural formula (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Structural formula (I) characterized by diazotizing the aniline derivative represented by (II) and then reducing it ▲ Numerical formulas, chemical formulas,
There are tables etc.▼(I) Manufacturing method of 2-fluoro-5-nitrophenylhydrazine represented by.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7385385A JPS61233656A (en) | 1985-04-08 | 1985-04-08 | 2-fluoro-5-nitrophenylhydrazine and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7385385A JPS61233656A (en) | 1985-04-08 | 1985-04-08 | 2-fluoro-5-nitrophenylhydrazine and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61233656A true JPS61233656A (en) | 1986-10-17 |
| JPH0578544B2 JPH0578544B2 (en) | 1993-10-29 |
Family
ID=13530125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7385385A Granted JPS61233656A (en) | 1985-04-08 | 1985-04-08 | 2-fluoro-5-nitrophenylhydrazine and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61233656A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0723953A1 (en) * | 1995-01-24 | 1996-07-31 | Hoechst Aktiengesellschaft | Process for the preparation of 2-fluorophenylhydrazine |
-
1985
- 1985-04-08 JP JP7385385A patent/JPS61233656A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0723953A1 (en) * | 1995-01-24 | 1996-07-31 | Hoechst Aktiengesellschaft | Process for the preparation of 2-fluorophenylhydrazine |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0578544B2 (en) | 1993-10-29 |
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