JPS60120869A - Production of aminopyrazole - Google Patents
Production of aminopyrazoleInfo
- Publication number
- JPS60120869A JPS60120869A JP22547983A JP22547983A JPS60120869A JP S60120869 A JPS60120869 A JP S60120869A JP 22547983 A JP22547983 A JP 22547983A JP 22547983 A JP22547983 A JP 22547983A JP S60120869 A JPS60120869 A JP S60120869A
- Authority
- JP
- Japan
- Prior art keywords
- aminopyrazole
- reaction
- hydrazine
- present
- solvent
- 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
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 4
- -1 BeC-butyl Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TYNVOQYGXDUHRX-UHFFFAOYSA-N 1-nitropyrazole Chemical compound [O-][N+](=O)N1C=CC=N1 TYNVOQYGXDUHRX-UHFFFAOYSA-N 0.000 description 1
- PEIBTJDECFEPAF-UHFFFAOYSA-N 2-methoxyprop-2-enenitrile Chemical compound COC(=C)C#N PEIBTJDECFEPAF-UHFFFAOYSA-N 0.000 description 1
- LCZCQSVHANMYNX-UHFFFAOYSA-N 3-butoxyprop-2-enenitrile Chemical compound CCCCOC=CC#N LCZCQSVHANMYNX-UHFFFAOYSA-N 0.000 description 1
- VIHRIIARIFUQLC-UHFFFAOYSA-N 3-hydrazinylpropanenitrile Chemical compound NNCCC#N VIHRIIARIFUQLC-UHFFFAOYSA-N 0.000 description 1
- MZRUFMBFIKGOAL-UHFFFAOYSA-N 5-nitro-1h-pyrazole Chemical compound [O-][N+](=O)C1=CC=NN1 MZRUFMBFIKGOAL-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
本発明は、アミノピラゾールの新規な製法に関するもの
である。さらに詳しくは本発明は、３−アミノピラゾー
ルと５−アミノピラゾールとの互変異性体の製法を提供
するものである。なお本明細書において、該互変異性体
を３（５）−アミノピラゾールと称す。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel method for producing aminopyrazoles. More specifically, the present invention provides a method for producing tautomers of 3-aminopyrazole and 5-aminopyrazole. In this specification, this tautomer is referred to as 3(5)-aminopyrazole.
従来、医薬、農薬などの合成中間体として重要な化合物
である６（５）−アミノピラゾールの製法につき９種々
提案がなされている。Up to now, nine different proposals have been made regarding methods for producing 6(5)-aminopyrazole, which is an important compound as a synthetic intermediate for pharmaceuticals, agricultural chemicals, and the like.
Ｏｒｇ、 ８ｙｎｔｈ、 Ｖ 五ム（１９７３）には、
β−シアノエチルヒドラジンをエタノール中において硫
酸で処理し、得られる６−アミノ−６−ピラゾリン硫酸
［−Ｐ−トルエンスルホン酸クロライドと処理し。Org, 8ynth, V. Gomu (1973),
β-cyanoethylhydrazine is treated with sulfuric acid in ethanol and the resulting 6-amino-6-pyrazoline sulfate [-P-toluenesulfonic acid chloride.
３（５）−アミノピラゾールを製造する方法につき開示
されている。A method for producing 3(5)-aminopyrazole is disclosed.
また、Ｓｙｙ＜ｔｈｅｓｉｓ ５巻Ｐ２９４（１９７３
）には。Also, Syy<thesis Volume 5 P294 (1973
)for.
ピラゾールをニトロ化し、得られるＮ−ニトロピラゾー
ルを熱的異性化によシ３−ニトロピラゾールとし９次い
でニトロ基を還元することによる３（５）−アミノピラ
ゾールの製法につき、提案がなされている。It has been proposed to produce 3(5)-aminopyrazole by nitrating pyrazole, thermally isomerizing the resulting N-nitropyrazole to give 3-nitropyrazole, and then reducing the nitro group.
しかしこれら公知の方法は、いずれも工程、が長く煩雑
である上、原料も高価である。などの欠点を有している
。However, all of these known methods require long and complicated steps, and the raw materials are also expensive. It has drawbacks such as:
本発明者らは、３（５）−アミノピラゾールの工業的有
利な製法を確立することを目的とし、鋭意研究を行った
。その結果、安価に入手できる６−アルコキシアクリロ
ニトリルとヒドラジンを反応させれば、一段でしかも高
収率にて３（５）−アミノピラゾールを合成できること
を見い出し。The present inventors conducted extensive research with the aim of establishing an industrially advantageous manufacturing method for 3(5)-aminopyrazole. As a result, they discovered that 3(5)-aminopyrazole could be synthesized in a single step and in high yield by reacting 6-alkoxyacrylonitrile, which is available at low cost, with hydrazine.
本発明を完成するに到った。The present invention has now been completed.
本発明の原料である６−アルコキシアクリロニトリルは
、一般式ＲＯＣＲ＝ ＣＨＣＮで示すことができる。数
式において、Ｒはメチル、エチル＋ ｎ −プロピル、
１−プロピル、ｎ−ブチル、ｉ−ブチル、ＢｅＣ−ブチ
ル、 ｔｅｒｔ−ブチル、ｎ−ペンチル。6-alkoxyacrylonitrile, which is a raw material of the present invention, can be represented by the general formula ROCR=CHCN. In the formula, R is methyl, ethyl + n-propyl,
1-propyl, n-butyl, i-butyl, BeC-butyl, tert-butyl, n-pentyl.
ｎ−ヘキシル、ｎ−ヘプチル、ｎ−オクチルなどの如き
炭素数１〜８を有するアルキル基を挙げることができる
。これらのアルキル基には２反応を阻害しない置換基２
例えばアルコキシ基、ハロゲン原子などの置換基を有す
こともできる。Mention may be made of alkyl groups having 1 to 8 carbon atoms such as n-hexyl, n-heptyl, n-octyl and the like. These alkyl groups contain substituents 2 that do not inhibit the reaction.
For example, it may have a substituent such as an alkoxy group or a halogen atom.
本発明のもう一方の原料であるヒドラジンは。Hydrazine is the other raw material of the present invention.
それ自体でも使用に供すことができるが２通常取扱いの
容易な抱水ヒドラジンを使用するのが好ましい。また、
ヒドラジンの塩酸塩、硫酸塩、硝酸塩あるいはリン酸塩
などの塩類の形態で使用することもできる。これらヒド
ラジンの塩を使用する場合には、予じめアルカリで中和
しておくか、あるいは反応液中にアルカリを加えて、ヒ
ドラジンの塩を中和させる。Although it can be used as such, it is usually preferable to use hydrazine hydrate, which is easy to handle. Also,
It can also be used in the form of salts such as hydrazine hydrochloride, sulfate, nitrate or phosphate. When using these hydrazine salts, they are neutralized in advance with an alkali, or an alkali is added to the reaction solution to neutralize the hydrazine salts.
ヒドラジンは、′５−アルコキシアクリロニトリル１モ
ルに対し９通常１モル以上、好ましくけ１〜５モル程度
使用される。Hydrazine is used in an amount of usually 1 mol or more, preferably 1 to 5 mol, per 1 mol of '5-alkoxyacrylonitrile.
本発明の反応は、無溶媒下に行うこともできるが・反応
に不活性な溶媒中で行うこともできる。The reaction of the present invention can be carried out without a solvent, but can also be carried out in a solvent that is inert to the reaction.
使用に供される溶媒の具体例としては、メタノール、エ
タノール、フロパノール、ブタノール、エチレングリコ
ールなどのアルコール系溶媒；ジエチルエーテル、ジメ
トキシエタン、ジオキサン。Specific examples of solvents that can be used include alcoholic solvents such as methanol, ethanol, furopanol, butanol, and ethylene glycol; diethyl ether, dimethoxyethane, and dioxane.
テトラヒドロフランなどのエーテル系溶媒；ベンゼン、
トルエン、キシレン、ヘキサン、ヘプタン。Ether solvents such as tetrahydrofuran; benzene,
Toluene, xylene, hexane, heptane.
シクロヘキサンなどの炭化水素系溶媒；塩化メチレン、
クロロホルム、四塩化炭素、ジクロロエタンなどのハロ
ゲン化炭化水素系溶媒；酢酸メチル。Hydrocarbon solvents such as cyclohexane; methylene chloride,
Halogenated hydrocarbon solvents such as chloroform, carbon tetrachloride, and dichloroethane; methyl acetate.
酢酸エチル、酢酸ブチルなどのエステル系溶媒；さらに
はアキトニトリルジメチルスルホキシド。Ester solvents such as ethyl acetate and butyl acetate; and aquitonitrile dimethyl sulfoxide.
ジメチルホルムアミドおよび水などを例示することがで
きる。これらの中でも２％にアルコール系溶媒、あるい
はアルコール系溶媒と他の溶媒との混合溶媒の使用が好
ましい。Examples include dimethylformamide and water. Among these, it is preferable to use an alcohol solvent or a mixed solvent of an alcohol solvent and another solvent at 2%.
本発明の反応は室温程度の温和な条件でも進行するが、
加熱により反応速度を高めることができ。Although the reaction of the present invention proceeds under mild conditions around room temperature,
The reaction rate can be increased by heating.
通常６０〜１００℃の温度、で行うことができる。It can be carried out usually at a temperature of 60 to 100°C.
反応終了後１例えば濾過、濃縮、抽出、再結晶あるいは
、昇華などの操作を適宜採用することにより、目的物の
３（５）−アミノピラゾールを単離・精製することがで
きる。After the reaction is completed, the target product, 3(5)-aminopyrazole, can be isolated and purified by appropriately employing operations such as filtration, concentration, extraction, recrystallization, or sublimation.
次に９本発明の実施例を挙げる。Next, nine examples of the present invention will be described.
実施例１
冷却管、温度計つき内容積５０ｍｇのフラスコにろ−メ
トキシアクリロニトリル１６．６ｆと１００ｗｔ％抱水
ヒドラジン１２．Ｏｆを仕込み、８０℃の温度で３時間
攪拌させ反応を行った。反応後、減圧蒸留により、１３
０℃／３ｇＨｙの無色透明な留分１１．８Ｆを得た。該
液体は、ＭＳ、ＮＭＲ。Example 1 16.6f of methoxyacrylonitrile and 100wt% hydrazine hydrate were placed in a 50mg flask equipped with a cooling tube and a thermometer. Of was charged, and the reaction was carried out by stirring at a temperature of 80° C. for 3 hours. After the reaction, 13
A colorless and transparent fraction 11.8F was obtained at 0°C/3gHy. The liquid is MS, NMR.
ＩＲにより、３（５）−アミノピラゾールであると同定
した。It was identified as 3(5)-aminopyrazole by IR.
実施例２
原料として３−ｎ−ブトキシアクリロニトリル２５．２
ｆと８０ｗｔ％抱水ヒドラジン１５．Ｏｆを用いた他
は、実施例１と同様の操作で実験を行った。Example 2 3-n-butoxyacrylonitrile as raw material 25.2
f and 80 wt% hydrazine hydrate15. The experiment was conducted in the same manner as in Example 1, except that Of was used.
その結果、１０．８ｐの３（５）−アミノピラゾールが
得られた。As a result, 10.8p of 3(5)-aminopyrazole was obtained.
実施例ろ
溶媒としてジメチルホルムアミド１０ｍ／を使用し、ま
た反応を１００℃の温度で１時間行った他は、実施例１
と何様の操作で実験を行った。その結果、１ ｏｉｌｔ
の３（５）−アミノピラゾールが得られた。Example Example 1 except that 10 m/dimethylformamide was used as the filtration solvent and the reaction was carried out at a temperature of 100°C for 1 hour.
The experiment was conducted using various operations. As a result, 1 oil
3(5)-aminopyrazole was obtained.
実施例４
溶媒としてメタノール１０ＷＬｌを使用し、また反応を
６０℃の温度で５時間行った他は、実施例１と同様の操
作で実験を行った。その結果、１０．５１の３（５）−
アミノピラゾールが得られた。Example 4 An experiment was carried out in the same manner as in Example 1, except that 10 WLl of methanol was used as the solvent and the reaction was carried out at a temperature of 60° C. for 5 hours. As a result, 10.51 of 3(5)-
Aminopyrazole was obtained.
特許出願人 宇部興産株式会社Patent applicant: Ube Industries Co., Ltd.
Claims (1)
せることを特徴とするアミノピラゾールの製法。A method for producing aminopyrazole, which comprises reacting 6-alkoxyacrylonitrile with hydrazine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22547983A JPS60120869A (en) | 1983-12-01 | 1983-12-01 | Production of aminopyrazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22547983A JPS60120869A (en) | 1983-12-01 | 1983-12-01 | Production of aminopyrazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60120869A true JPS60120869A (en) | 1985-06-28 |
| JPH0421666B2 JPH0421666B2 (en) | 1992-04-13 |
Family
ID=16829962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22547983A Granted JPS60120869A (en) | 1983-12-01 | 1983-12-01 | Production of aminopyrazole |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60120869A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0242687A2 (en) * | 1986-04-17 | 1987-10-28 | Bayer Ag | Process for the preparation of 1-aryl-5-amino-pyrazoles |
| DE4333659C2 (en) * | 1993-10-02 | 2003-11-06 | Guenter Ege | 4-arylmethyl-1H-pyrazol-3-amines, their salts and process for their preparation |
-
1983
- 1983-12-01 JP JP22547983A patent/JPS60120869A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0242687A2 (en) * | 1986-04-17 | 1987-10-28 | Bayer Ag | Process for the preparation of 1-aryl-5-amino-pyrazoles |
| DE4333659C2 (en) * | 1993-10-02 | 2003-11-06 | Guenter Ege | 4-arylmethyl-1H-pyrazol-3-amines, their salts and process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0421666B2 (en) | 1992-04-13 |
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