JP2873509B2 - Method for producing 2-chloro-4-pyridinemethanol - Google Patents
Method for producing 2-chloro-4-pyridinemethanolInfo
- Publication number
- JP2873509B2 JP2873509B2 JP3008405A JP840591A JP2873509B2 JP 2873509 B2 JP2873509 B2 JP 2873509B2 JP 3008405 A JP3008405 A JP 3008405A JP 840591 A JP840591 A JP 840591A JP 2873509 B2 JP2873509 B2 JP 2873509B2
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- pyridinemethanol
- reaction
- cyanopyridine
- producing
- 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.)
- Expired - Fee Related
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は各種の医薬品及び農薬の
製造原料として有用な２−クロル−４−ピリジンメタノ
ールを製造する方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing 2-chloro-4-pyridinemethanol which is useful as a raw material for producing various pharmaceuticals and agricultural chemicals.
【０００２】[0002]
【従来の技術】２−クロル−４−ピリジンメタノールは
医薬品及び農薬の製造原料として有用な化合物であり、
例えば、特公平１−４１１５０号公報に記載された方法
により有用な医薬品の製造中間体である２−クロル−
（１−ピペリジノメチル）ピリジンに変換される。2. Description of the Related Art 2-Chloro-4-pyridinemethanol is a compound useful as a raw material for producing pharmaceuticals and agricultural chemicals.
For example, 2-chloro- which is an intermediate for producing a useful drug by the method described in Japanese Patent Publication No. 41150/1989.
Converted to (1-piperidinomethyl) pyridine.
【０００３】従来、２−クロル−４−ピリジンメタノー
ルの製造方法としては、２−クロル−４−メチルピリジ
ン−Ｎ−オキサイドに無水酢酸を作用させて２−クロル
−４−アセトキシメチルピリジンに変換した後に、これ
を加水分解する方法が知られている（薬学雑誌、81: 61
6-615 、1961）。しかし、該方法によれば比較的多量の
副生物が生成するという問題があった。従って、さらに
効率のよい２−クロル−４−ピリジンメタノールの製造
方法の開発が望まれていた。Conventionally, as a method for producing 2-chloro-4-pyridinemethanol, 2-chloro-4-methylpyridine-N-oxide was reacted with acetic anhydride to convert it to 2-chloro-4-acetoxymethylpyridine. Later, a method of hydrolyzing it is known (Pharmaceutical Journal, 81:61).
6-615, 1961). However, this method has a problem that a relatively large amount of by-products is generated. Therefore, development of a more efficient method for producing 2-chloro-4-pyridinemethanol has been desired.
【０００４】本発明者は、２−クロル−４−シアノピリ
ジンを２−クロル−４−ピリジンメタノールの製造原料
として選択し、該製造原料を水素添加することにより２
−クロル−４−ピリジンメタノールを効率よく製造すべ
く検討していた。しかし、水素添加の条件によってはピ
リジン核に置換した塩素原子が脱離したり、シアノ基の
加水分解が進行する等の不都合が生じ、水素添加により
直接２−クロル−４−ピリジンメタノールを製造するこ
とができないという問題があった。The present inventors have selected 2-chloro-4-cyanopyridine as a raw material for producing 2-chloro-4-pyridinemethanol, and hydrogenated the raw material to obtain 2-chloro-4-cyanopyridine.
-Chloro-4-pyridinemethanol was studied for efficient production. However, depending on the hydrogenation conditions, disadvantages such as elimination of the chlorine atom substituted on the pyridine nucleus and progress of hydrolysis of the cyano group occur. There was a problem that can not be.
【０００５】[0005]
【発明が解決しようとする課題】従って本発明は、選択
的かつ高収率で２−クロル−４−ピリジンメタノールを
製造する方法を提供することを目的とする。Accordingly, an object of the present invention is to provide a method for producing 2-chloro-4-pyridinemethanol selectively and with high yield.
【０００６】[0006]
【課題を解決するための手段】本発明者は上記の課題を
解決すべく鋭意検討した結果、水素化触媒の存在下に特
定の条件で２−クロル−４−シアノピリジンを水素化す
ると、ピリジン核からの塩素原子の脱離が生じないの
で、ほぼ選択的に２−クロル−４−ピリジノメタノール
を製造することができること、及び反応系中に副産物と
して生成する２−クロル−４−アミノメチルピリジンを
さらに化学変換することにより高収率で目的とする２−
クロル−４−ピリジンメタノールを製造できることを見
出し、本発明を完成するに至った。すなわち本発明は、
酸性水溶液中で２−クロル−４−シアノピリジンを水素
化触媒の存在下に反応温度４０℃以下で水素化して２−
クロル−４−ピリジンメタノールを製造する方法を提供
するものである。さらに本発明により、酸性水溶液中で
２−クロル−４−シアノピリジンを水素化触媒の存在下
に反応温度４０℃以下で水素化し、得られた反応液をさ
らに酸性水溶液中で亜硝酸塩類で処理して２−クロル−
４−ピリジンメタノールを製造する方法が提供される。The present inventors have conducted intensive studies to solve the above-mentioned problems. As a result, when 2-chloro-4-cyanopyridine is hydrogenated under specific conditions in the presence of a hydrogenation catalyst, pyridine is obtained. Since elimination of a chlorine atom from the nucleus does not occur, 2-chloro-4-pyridinomethanol can be produced almost selectively, and 2-chloro-4-aminomethyl produced as a by-product in the reaction system By subjecting pyridine to further chemical conversion, the desired 2-
They have found that chloro-4-pyridinemethanol can be produced, and have completed the present invention. That is, the present invention
Hydrogenation of 2-chloro-4-cyanopyridine in an acidic aqueous solution at a reaction temperature of 40 ° C. or less in the presence of a hydrogenation catalyst to give 2-chloro-4-cyanopyridine
The present invention provides a method for producing chloro-4-pyridinemethanol. Further, according to the present invention, 2-chloro-4-cyanopyridine is hydrogenated in an acidic aqueous solution at a reaction temperature of 40 ° C. or lower in the presence of a hydrogenation catalyst, and the obtained reaction solution is further treated with nitrite in an acidic aqueous solution. Then 2-chloro-
A method for producing 4-pyridinemethanol is provided.
【０００７】出発原料として使用される２−クロル−４
−シアノピリジンは、４−メチルピリジンのアンモ酸化
によって工業生産されている４−シアノピリジンを、Ｎ
−オキサイド化及びクロル化することにより容易に製造
される文献記載の化合物である（The Journal of Organ
ic Chemistry、26: 668 、1961 及び薬学雑誌、81:120
4-1206 、1961参照）。2-chloro-4 used as starting material
-Cyanopyridine is obtained by converting 4-cyanopyridine industrially produced by ammoxidation of 4-methylpyridine to N-
-A compound described in the literature that is easily produced by oxidation and chlorination (The Journal of Organ
ic Chemistry, 26: 668, 1961 and Pharmaceutical Journal, 81: 120
4-1206, 1961).
【０００８】本発明の方法によれば、上記の２−クロル
−４−シアノピリジンの水素化は酸性水溶液中で行われ
る。酸性水溶液としてはpHが約１以下の酸性水溶液を挙
げることができ、例えば塩酸、硫酸等の鉱酸を水で希釈
したものを挙げることができる。酸性水溶液中に含有さ
れる酸の量は、２−クロル−４−シアノピリジンに対し
て１〜１０モルの範囲が好ましく、水の使用量は使用さ
れる酸に対して0.５〜１０重量部の範囲が好ましい。酸
性水溶液中に含まれる酸の量が２−クロル−４−シアノ
ピリジンに対して１モルを下回ると、水素添加が進行し
難く収率が悪くなる傾向があり、酸の量が２−クロル−
４−シアノピリジンに対して１０モルを上回ると、生成
した２−クロル−４−ピリジンメタノールの酸付加塩か
ら２−クロル−４−ピリジンメタノールを遊離塩基とし
て単離する際に使用する中和剤の使用量が多くなり、さ
らに中和で多量の無機塩が生成するので２−クロル−４
−ピリジンメタノールの分離工程が煩雑になり好ましく
ない。According to the process of the present invention, the hydrogenation of 2-chloro-4-cyanopyridine is carried out in an acidic aqueous solution. Examples of the acidic aqueous solution include an acidic aqueous solution having a pH of about 1 or less, for example, a solution obtained by diluting a mineral acid such as hydrochloric acid or sulfuric acid with water. The amount of the acid contained in the acidic aqueous solution is preferably in the range of 1 to 10 mol based on 2-chloro-4-cyanopyridine, and the amount of water used is 0.5 to 10% by weight based on the acid used. The range of parts is preferred. When the amount of the acid contained in the acidic aqueous solution is less than 1 mol with respect to 2-chloro-4-cyanopyridine, the hydrogenation does not easily proceed and the yield tends to be poor.
If it exceeds 10 moles with respect to 4-cyanopyridine, a neutralizing agent to be used when isolating 2-chloro-4-pyridinemethanol as a free base from the formed acid addition salt of 2-chloro-4-pyridinemethanol Is increased, and a large amount of inorganic salt is formed by neutralization.
-The process of separating pyridine methanol is complicated, which is not preferable.
【０００９】水素化触媒としては、アルミナ、ケイソウ
土、白土、又は活性炭等に、白金、パラジウム等の貴金
属を0.２〜２０重量％になる様に担持させた貴金属触媒
や、ラネーニッケル合金またはラネーコバルト合金を常
法により展開したラネーニッケル触媒やラネーコバルト
触媒等のラネー触媒類を挙げることができる。これらの
触媒のうち、触媒価格や工業的な取扱い等の観点からは
ラネーニッケル触媒が好ましく、収率及び２−クロル−
４−ピリジンメタノールの選択性の観点からは貴金属触
媒が好ましい。As the hydrogenation catalyst, a noble metal catalyst in which a noble metal such as platinum or palladium is supported on alumina, diatomaceous earth, terra alba, activated carbon or the like to a concentration of 0.2 to 20% by weight, a Raney nickel alloy or a Raney nickel Raney catalysts such as a Raney nickel catalyst and a Raney cobalt catalyst obtained by developing a cobalt alloy by an ordinary method can be used. Among these catalysts, Raney nickel catalyst is preferred from the viewpoint of catalyst price and industrial handling, and the yield and 2-chloro-
A noble metal catalyst is preferred from the viewpoint of selectivity for 4-pyridinemethanol.
【００１０】前記水素化触媒の使用量は、原料である２
−クロル−４−シアノピリジンに対して、ラネー触媒の
場合に５〜５０重量％、貴金属触媒の場合には0.１〜２
０重量％の範囲とすればよい。[0010] The amount of the hydrogenation catalyst used is 2
5 to 50% by weight with respect to chloro-4-cyanopyridine in the case of a Raney catalyst and 0.1 to 2 in the case of a noble metal catalyst
The range may be 0% by weight.
【００１１】本発明の方法によれば、水素化反応は反応
温度４０℃以下、好ましくは０〜２０℃の範囲内で行わ
れる。反応温度が４０℃を越える場合には２−クロル−
４−シアノピリジンの４位シアノ基が酸性水溶液中で加
水分解されたり、ピリジン核の２位で脱塩素化反応が進
行する等の不都合が生じる。また、反応圧力としては常
圧下ないしは加圧下のいずれでもよいが、反応速度や操
作性の観点から５ないし１００気圧の水素圧で反応を行
うことが好ましい。According to the method of the present invention, the hydrogenation reaction is carried out at a reaction temperature of 40 ° C. or lower, preferably in the range of 0 to 20 ° C. When the reaction temperature exceeds 40 ° C, 2-chloro-
Inconveniences such as hydrolysis of the 4-position cyano group of 4-cyanopyridine in an acidic aqueous solution and progress of the dechlorination reaction at the 2-position of the pyridine nucleus occur. The reaction pressure may be either normal pressure or pressurization, but it is preferable to carry out the reaction at a hydrogen pressure of 5 to 100 atm from the viewpoint of reaction rate and operability.
【００１２】本発明の方法によれば、２−クロル−４−
シアノピリジンの水素添加は通常１ないし５時間で終了
し、原料である２−クロル−４−シアノピリジンがほぼ
消費され、目的とする２−クロル−４−ピリジンメタノ
ールの酸付加塩を主生成物として含む反応液が得られ
る。該反応液から２−クロル−４−ピリジンメタノール
またはその酸付加塩を単離するには、反応液から水素化
触媒を常法により除去した後に、濾液をアルカリ金属の
水酸化物若しくは炭酸塩等の塩基を用いてpH２程度に
し、必要に応じて水を留去した後に、ブタノール、トル
エン、クロロホルム等の有機溶媒で抽出すればよい。こ
の抽出液を常法により濃縮し冷却すると２−クロル−４
−ピリジンメタノール酸付加塩が得られる。また、濾液
をアルカリ金属の水酸化物若しくは炭酸塩等の塩基を用
いてアルカリ性にした後に、ブタノール、トルエン、ク
ロロホルム等の有機溶媒で抽出し、溶媒を留去して得ら
れた油層を蒸留することにより、遊離の２−クロル−４
−ピリジンメタノールが得られる。According to the method of the present invention, 2-chloro-4-
The hydrogenation of cyanopyridine is usually completed in 1 to 5 hours, the raw material 2-chloro-4-cyanopyridine is almost consumed, and the desired acid addition salt of 2-chloro-4-pyridinemethanol is obtained as the main product. Is obtained. In order to isolate 2-chloro-4-pyridinemethanol or an acid addition salt thereof from the reaction solution, the hydrogenation catalyst is removed from the reaction solution by a conventional method, and the filtrate is washed with an alkali metal hydroxide or carbonate. The pH may be adjusted to about 2 using the above base, and water may be distilled off if necessary, followed by extraction with an organic solvent such as butanol, toluene and chloroform. The extract is concentrated and cooled by a conventional method to give 2-chloro-4.
-A pyridinemethanolic acid addition salt is obtained. Further, the filtrate is made alkaline with a base such as an alkali metal hydroxide or carbonate, and then extracted with an organic solvent such as butanol, toluene, and chloroform, and the oil layer obtained by distilling the solvent is distilled. Thus, free 2-chloro-4
-Pyridine methanol is obtained.
【００１３】上記の反応工程においては、目的とする２
−クロル−４−ピリジンメタノール以外に、２−クロル
−４−アミノメチルピリジンが副産物として通常２−ク
ロル−４−ピリジンメタノールに対して２５〜１６５重
量％以下で反応液に含有される。この様な反応液を、例
えば硫酸、塩酸等の酸の存在下に、例えば亜硝酸ナトリ
ウムや亜硝酸カリウム等の亜硝酸塩で処理することによ
り、副産物として生成した２−クロル−４−アミノメチ
ルピリジンを２−クロル−４−ピリジンメタノールに変
換することができる。酸の使用量としては２−クロル−
４−アミノメチルピリジンに対して１〜５モルの範囲が
好ましく、水の使用量は酸に対して１〜１０重量部であ
ることが好ましい。上記の酸のうち硫酸を使用すること
が好ましいが、硫酸の量が２−クロル−４−アミノメチ
ルピリジンに対して１モル未満になると反応が進行し難
く、収率が低下するという問題があり、５モルを越える
場合には亜硝酸塩から生じる窒素酸化物の量が多くなり
好ましくない。亜硝酸塩の使用量としては２−クロル−
４−アミノメチルピリジンに対して１〜５モルが収率の
面から好ましい。In the above reaction step, the desired 2
In addition to -chloro-4-pyridinemethanol, 2-chloro-4-aminomethylpyridine is usually contained as a by-product in the reaction solution in an amount of 25 to 165% by weight or less based on 2-chloro-4-pyridinemethanol. By treating such a reaction solution with a nitrite such as sodium nitrite or potassium nitrite in the presence of an acid such as sulfuric acid or hydrochloric acid, 2-chloro-4-aminomethylpyridine produced as a by-product can be obtained. It can be converted to 2-chloro-4-pyridinemethanol. The amount of acid used is 2-chloro-
The amount is preferably in the range of 1 to 5 mol based on 4-aminomethylpyridine, and the amount of water used is preferably 1 to 10 parts by weight based on the acid. Of the above acids, it is preferable to use sulfuric acid. However, when the amount of sulfuric acid is less than 1 mol with respect to 2-chloro-4-aminomethylpyridine, there is a problem that the reaction hardly proceeds and the yield decreases. If it exceeds 5 moles, the amount of nitrogen oxides generated from nitrite increases, which is not preferable. The amount of nitrite used is 2-chloro-
From 1 to 5 mol is preferable from the viewpoint of the yield based on 4-aminomethylpyridine.
【００１４】[0014]
【発明の効果】本発明の方法よれば、２−クロル−４−
シアノピリジンから直接２−クロル−４−ピリジンメタ
ノールを製造することができる。さらに反応液中に副産
物として生成する２−クロル−４−アミノメチルピリジ
ンを２−クロル−４−ピリジンメタノールに変換するこ
とにより、例えば６０〜８０％の総収率で２−クロル−
４−ピリジンメタノールが得られるので有用である。According to the method of the present invention, 2-chloro-4-
2-Chloro-4-pyridinemethanol can be produced directly from cyanopyridine. Further, 2-chloro-4-aminomethylpyridine produced as a by-product in the reaction solution is converted to 2-chloro-4-pyridinemethanol, for example, to give 2-chloro-4-aminomethyl with a total yield of 60 to 80%.
This is useful because 4-pyridinemethanol is obtained.
【００１５】[0015]
【実施例】以下に本発明を実施例によりさらに具体的に
説明するが、本発明はこれらの実施例に限定されること
はない。EXAMPLES The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to these examples.
【００１６】実施例１容量１リットルの電磁攪拌式ガラ
スオートクレーブに２−クロル−４−シアノピリジン６
８ｇ、濃硫酸２２４ｇ、水２２４ｇ、及び５％パラジウ
ム炭素触媒3.５ｇを加え、容器内に水素ガスを導入して
５Kg/cm2、２０℃で反応を行った。反応が進行するにつ
れて水素圧が減少するので逐次水素を追加した。３時間
で反応を終了し、得られた反応物を濾過して触媒を濾去
した。濾液に１７１ｇの水を追加した後に無水炭酸カリ
ウムで中和し、クロロホルムで抽出した後に、抽出液を
ガスクロマトグラフィーで分析すると、２−クロル−４
−ピリジンメタノール４0.１ｇ（収率５7.４％）と２−
クロル−４−アミノメチルピリジン１5.８ｇ（収率２2.
８％）が含まれていた。EXAMPLE 1 2-Chloro-4-cyanopyridine 6 was placed in a 1 liter electromagnetically stirred glass autoclave.
8 g, 224 g of concentrated sulfuric acid, 224 g of water, and 3.5 g of a 5% palladium carbon catalyst were added, and hydrogen gas was introduced into the vessel to carry out a reaction at 5 kg / cm 2 at 20 ° C. Since the hydrogen pressure decreased as the reaction proceeded, hydrogen was added sequentially. The reaction was completed in 3 hours, and the obtained reaction product was filtered to remove the catalyst by filtration. After adding 171 g of water to the filtrate, neutralizing with anhydrous potassium carbonate, extracting with chloroform, and analyzing the extract by gas chromatography, 2-chloro-4 was obtained.
-40.1 g of pyridinemethanol (yield 57.4%) and 2-
15.8 g of chloro-4-aminomethylpyridine (22.
8%).
【００１７】実施例２容量１リットルの電磁攪拌式ガラ
スオートクレーブに２−クロル−４−シアノピリジン８
３ｇ、濃硫酸８８ｇ、水３３６ｇ、及びラネーニッケル
触媒３３ｇを加え、容器内に水素ガスを導入して５Kg/c
m2、２０℃で反応を行った。反応が進行するにつれて水
素圧が減少するので逐次水素を追加した。５時間で反応
を終了し、実施例１と同様に処理したところ、抽出液に
は２−クロル−４−ピリジンメタノール２3.７ｇ（収率
２7.６％）と２−クロル−４−アミノメチルピリジン３
8.９ｇ（収率４5.６％）が含まれていた。EXAMPLE 2 2-Chloro-4-cyanopyridine 8 was added to a 1-liter electromagnetically stirred glass autoclave.
3 g, 88 g of concentrated sulfuric acid, 336 g of water, and 33 g of Raney nickel catalyst were added, and hydrogen gas was introduced into the vessel and 5 kg / c.
The reaction was performed at m 2 and 20 ° C. Since the hydrogen pressure decreased as the reaction proceeded, hydrogen was added sequentially. The reaction was completed in 5 hours, and the mixture was treated in the same manner as in Example 1. The extract contained 23.7 g (27.6% yield) of 2-chloro-4-pyridinemethanol and 2-chloro-4-aminomethyl. Pyridine 3
It contained 8.9 g (45.6% yield).
【００１８】実施例３実施例１と同一の条件で反応させ
た得られた反応液に、３５％亜硝酸ナトリウム水溶液３
７ｇを反応温度零下５℃〜０℃で５時間かけて滴下し、
同温度でひき続き２時間反応させた。得られた反応液を
水酸化ナトリウムで中和し、ついでｎ−ブタノールで抽
出した。得られた有機層から溶媒を留去した後に、蒸留
によりb.p.１２３℃の２−クロル−４−ピリジンメタノ
ール５7.７ｇ（収率７8.３％：ガスクロマトグラフィー
による純度９５％）を得た。Example 3 A reaction solution obtained under the same conditions as in Example 1 was added to a 35% aqueous sodium nitrite solution
7 g was added dropwise over 5 hours at a reaction temperature of 5 ° C to 0 ° C under zero temperature,
The reaction was continued at the same temperature for 2 hours. The obtained reaction solution was neutralized with sodium hydroxide, and then extracted with n-butanol. After evaporating the solvent from the obtained organic layer, 57.7 g (yield: 78.3%, purity by gas chromatography: 95%) of 2-chloro-4-pyridinemethanol having a bp of 123 ° C. was obtained by distillation.
【００１９】比較例１反応温度を６０℃とした以外は実
施例１と同様に水素化を行い、実施例１と同様の処理を
行ったところ、抽出液には４−ピリジンメタノール１4.
６ｇ（収率２7.５％）と４−アミノメチルピリジン１7.
８ｇ（収率３3.９％）が含まれていたが、２−クロル−
４−ピリジンメタノールと２−クロル−４−アミノメチ
ルピリジンの生成は認められなかった。Comparative Example 1 Hydrogenation was carried out in the same manner as in Example 1 except that the reaction temperature was changed to 60 ° C., and the same treatment as in Example 1 was carried out.
6 g (yield 27.5%) and 4-aminomethylpyridine 17.
8g (yield 33.9%), but 2-chloro-
No formation of 4-pyridinemethanol and 2-chloro-4-aminomethylpyridine was observed.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭48−29784（ＪＰ，Ａ) 特開 平１−230556（ＪＰ，Ａ) (58)調査した分野(Int.Cl.6，ＤＢ名) C07D 213/61 ＣＡ（ＳＴＮ)────────────────────────────────────────────────── ─── Continuation of front page (56) References JP-A-48-29784 (JP, A) JP-A-1-230556 (JP, A) (58) Fields investigated (Int. Cl. 6 , DB name) C07D 213/61 CA (STN)
Claims (2)
ピリジンを水素化触媒の存在下に反応温度４０℃以下で
水素化して２−クロル−４−ピリジンメタノールを製造
する方法。1. A method for producing 2-chloro-4-pyridinemethanol by hydrogenating 2-chloro-4-cyanopyridine in an acidic aqueous solution at a reaction temperature of 40 ° C. or lower in the presence of a hydrogenation catalyst.
ピリジンを水素化触媒の存在下に反応温度４０℃以下で
水素化し、得られた反応液をさらに酸性水溶液中で亜硝
酸塩類で処理して２−クロル−４−ピリジンメタノール
を製造する方法。2. Hydrogenation of 2-chloro-4-cyanopyridine in an acidic aqueous solution at a reaction temperature of 40 ° C. or lower in the presence of a hydrogenation catalyst, and the resulting reaction solution is further treated with nitrites in an acidic aqueous solution. To produce 2-chloro-4-pyridinemethanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3008405A JP2873509B2 (en) | 1991-01-28 | 1991-01-28 | Method for producing 2-chloro-4-pyridinemethanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3008405A JP2873509B2 (en) | 1991-01-28 | 1991-01-28 | Method for producing 2-chloro-4-pyridinemethanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04243867A JPH04243867A (en) | 1992-08-31 |
| JP2873509B2 true JP2873509B2 (en) | 1999-03-24 |
Family
ID=11692258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3008405A Expired - Fee Related JP2873509B2 (en) | 1991-01-28 | 1991-01-28 | Method for producing 2-chloro-4-pyridinemethanol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2873509B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3071340B2 (en) * | 1993-06-02 | 2000-07-31 | セントラル硝子株式会社 | Method for producing 2-chloro-pyridinemethanol |
| CA2415842A1 (en) | 2000-08-25 | 2002-02-28 | Michael Mellor | Process for the preparation of 2-aminoethylpyridines |
-
1991
- 1991-01-28 JP JP3008405A patent/JP2873509B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04243867A (en) | 1992-08-31 |
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