JP3698326B2 - Process for producing 5-imidazol-1-yl-2-nitroaniline - Google Patents
Process for producing 5-imidazol-1-yl-2-nitroaniline Download PDFInfo
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- JP3698326B2 JP3698326B2 JP22909994A JP22909994A JP3698326B2 JP 3698326 B2 JP3698326 B2 JP 3698326B2 JP 22909994 A JP22909994 A JP 22909994A JP 22909994 A JP22909994 A JP 22909994A JP 3698326 B2 JP3698326 B2 JP 3698326B2
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- nitroaniline
- imidazol
- reaction
- halogeno
- imidazole
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- CVGWDTJIPMBOKL-UHFFFAOYSA-N 5-imidazol-1-yl-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC(N2C=NC=C2)=C1 CVGWDTJIPMBOKL-UHFFFAOYSA-N 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 239000002798 polar solvent Substances 0.000 claims description 7
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims description 4
- ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000004811 liquid chromatography Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- RMIFLIVHJLREFJ-UHFFFAOYSA-N 5-bromo-2-nitroaniline Chemical compound NC1=CC(Br)=CC=C1[N+]([O-])=O RMIFLIVHJLREFJ-UHFFFAOYSA-N 0.000 description 1
- PEDMFCHWOVJDNW-UHFFFAOYSA-N 5-fluoro-2-nitroaniline Chemical compound NC1=CC(F)=CC=C1[N+]([O-])=O PEDMFCHWOVJDNW-UHFFFAOYSA-N 0.000 description 1
- FQPPKORVTBLTBX-UHFFFAOYSA-N 5-iodo-2-nitroaniline Chemical compound NC1=CC(I)=CC=C1[N+]([O-])=O FQPPKORVTBLTBX-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003925 brain function Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UMLFDVOHVJPDIZ-UHFFFAOYSA-N hydron;6-imidazol-1-yl-7-nitro-1,4-dihydroquinoxaline-2,3-dione;chloride Chemical compound Cl.[O-][N+](=O)C1=CC=2NC(=O)C(=O)NC=2C=C1N1C=CN=C1 UMLFDVOHVJPDIZ-UHFFFAOYSA-N 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】
【産業上の利用分野】
本発明は、薬理作用を有する６−（１−Ｈ−イミダゾール−１−イル）−７−ニトロ−２，３−（１Ｈ，４Ｈ）−キノキサリンジオン用の中間体５−イミダゾール−１−イル−２−ニトロアニリンの製造方法に関する。
【０００２】
【従来の技術】
５−イミダゾール−１−イル−２−ニトロアニリンは、脳機能改善剤として知られるＷＯ９２／０７８４７に記載の６−（１−Ｈ−イミダゾール−１−イル）−７−ニトロ−２，３−（１Ｈ，４Ｈ）−キノキサリンジオンの重要な中間体である。５−イミダゾール−１−イル−２−ニトロアニリンの合成法に関しては、特開平３−１４５７９およびＪｏｕｒｎａｌ ｏｆ Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍｉｓｔｒｙ，１９９２年，３５巻，４４５５−４４６３頁に、過剰量のイミダゾールを用いて、Ｎ，Ｎ−ジメチルホルムアミドを反応溶媒に使用するか、または無溶媒下において加熱することによる製造方法の記載がなされている。
【０００３】
【発明が解決しようとする課題】
従来の方法によると無溶媒下で反応を行うためにイミダゾールを６モル当量以上使用し、且つ反応温度として約１８０℃の高温を必要とする。イミダゾールの沸点は２５７℃（７６０ｍｍＨｇ）であるが、昇華性を有しており、このような方法では仕込み効率の低下や装置の閉塞の問題がある。またＮ，Ｎ−ジメチルホルムアミドを溶媒に用いると副生物が多く、収率が低いという問題がある。
【０００４】
【課題を解決するための手段】
本発明者らは、５−イミダゾール−１−イル−２−ニトロアニリンの簡便な製造方法を見出すべく鋭意検討を重ねた結果、本発明に到達することが出来た。即ち本発明は、
（１）イミダゾールと５−ハロゲノ−２−ニトロアニリンをヘテロ環を有する非プロトン性極性溶媒中にて反応させることを特徴とする５−イミダゾール−１−イル−２−ニトロアニリンの製造方法
（２）イミダゾールと５−ハロゲノ−２−ニトロアニリンとをモル比１：１〜１０比で反応させる前項（１）記載の製造方法
（３）ヘテロ環を有する非プロトン性極性溶媒がＮ−メチル−２−ピロリドン、１，３−ジメチル−２−イミダゾリジノンである前項（１）記載の製造方法
（４）ヘテロ環を有する非プロトン性極性溶媒の使用量が５−ハロゲノ−２−ニトロアニリンの１〜３０重量倍である前項（１）記載の製造方法
（５）反応温度が１００〜２１０℃である前項（１）記載の製造方法
（６）イミダゾ−ルと５−ハロゲノ−２−ニトロアニリンとの反応を塩基の存在下に行う前項（１）記載の製造方法
（７）塩基の使用量が５−ハロゲノ−２−ニトロアニリンのモル量に対して０．１〜５モル当量である前項（６）記載の製造方法
に関する。
【０００５】
本発明で使用する５−ハロゲノ−２−ニトロアニリンとしては、例えば５−フロロ−２−ニトロアニリン、５−クロロ−２−ニトロアニリン、５−ブロモ−２−ニトロアニリン、５−ヨウド−２−ニトロアニリンが挙げられる。使用する溶媒はヘテロ環を有する非プロトン性極性溶媒として、Ｎ−メチル−２−ピロリドン、１，３−ジメチル−２−イミダゾリジノンが好ましい。２種類の混合溶媒としても使用できる。溶媒の使用量は、基質である５−ハロゲノ−２−ニトロアニリンの１〜３０重量倍で、好ましくは２〜１０重量倍である。本発明方法を実施するには所定の溶媒中にイミダゾールを５−ハロゲノ−２−ニトロアニリンのモル量の１〜１０モル当量溶解せしめ、撹拌しつつ５−ハロゲノ−２−ニトロアニリンを所定量添加し、加熱することにより徐々に反応系中の温度を好ましくは１００〜２１０℃に昇温させて、より好ましくは１５０〜２００℃で５〜１５時間程度撹拌を行えば良い。
【０００６】
上記の反応条件下では反応完結に長時間を必要とするため苛性ソーダ、苛性カリ、炭酸ソーダ、炭酸カリ、重曹等の塩基を５−ハロゲノ−２−ニトロアニリンに対し０．１〜５モル当量加えて、好ましくは０．２〜３モル当量加えることにより短時間のうちに反応を完結させることが出来る。
【０００７】
反応完結後は使用した溶媒の３〜１５重量倍の水中に反応液を注入することにより５−イミダゾール−１−イル−２−ニトロアニリンを析出させ反応系中より回収し、良く水洗、濾過、乾燥することにより、純度の高いものを得ることが出来る。
【０００８】
このようにして目的物である５−イミダゾール−１−イル−２−ニトロアニリンを良好の収率で純度の高いものを得ることが出来る。この方法によるとイミダゾールの昇華を抑えて、高温下に加熱することが可能で短時間に効率よく、しかも副生物の生成を抑制しながら製造することが出来る。
純度は、液体クロマトグラフィ−で容易に測定することができる。
【０００９】
【実施例】
以下、実施例により更に詳しく説明する。
【００１０】
実施例１
５０ｍｌのガラス製の四つ口フラスコにＮ−メチル−２−ピロリドン２０ｇ、イミダゾール４．０ｇ、５−クロロ−２−ニトロアニリン５．０ｇ、炭酸ナトリウム１．８ｇを取り、撹拌しながら温度１８０℃で反応を行った。６時間反応を行い、液クロで反応液を分析したところ原料の５−クロロ−２−ニトロアニリンが完全に消費されたのを確認した。水１００ｃｃに反応液を注入したところ不溶物分として５−イミダゾ−ル−１−イル−２−ニトロアニリンが析出した。濾過することにより粗生物として５−イミダゾ−ル−１−イル−２−ニトロアニリンが５．０２ｇ、収率８５％、液クロ純度９５．５％で得られた。
以下に液クロの分析条件を示す。
アセトニトリル：０．５％リン酸二水素カリウム＝４００：６００、
流速１．０ｍｌ／ｍｉｎ．、カラム温度 ４０℃
【００１１】
実施例２
１００ｍｌのガラス製の四つ口フラスコに１，３−ジメチル−２−イミダゾリジノン４０ｇ、イミダゾール２０．４ｇ、５−クロロ−２−ニトロアニリン３４．６ｇ、炭酸カリウム１６．６ｇを取り、撹拌しながら温度１８０℃で反応を行った。７時間反応を行い、液クロで反応液を分析したところ原料の５−クロロ−２−ニトロアニリンが完全に消費されたのを確認した。その後、水１２０ｃｃに反応液を注入したところ不溶物分として５−イミダゾ−ル−１−イル−２−ニトロアニリンが析出した。濾過することにより粗生物として５−イミダゾ−ル−１−イル−２−ニトロアニリンが３２．６ｇ、収率８０％、液クロ純度９７．３％で得られた。
【００１２】
実施例３
５０ｍｌのガラス製の四つ口フラスコにＮ−メチル−２−ピロリドン２０ｇ、イミダゾール４．０ｇ、５−クロロ−２−ニトロアニリン５．０ｇを取り、撹拌しながら温度１８０℃で反応を行った。６時間反応を行い、液クロで反応液を分析したところ５−イミダゾール−１−イル−２−ニトロアニリンが５８．５％、未反応の５−クロロ−２−ニトロアニリンが３５．３％であった。
【００１３】
比較例１
１００ｍｌのガラス製の四つ口フラスコにＮ，Ｎ−ジメチルホルムアミド６０ｍｌ、イミダゾール２７．２ｇ、５−クロロ−２−ニトロアニリン １７．３ｇを取り、撹拌しながら温度１６５℃で反応を行った。８時間反応を行い、液クロで反応液を分析したところ副生物を伴い５−イミダゾール−１−イル−２−ニトロアニリンが３８．５％、未反応の５−クロロ−２−ニトロアニリンが４０．５％、副生物２０％であった。
【００１４】
比較例２
５０ｍｌのガラス製の四つ口フラスコにイミダゾール１０ｇ、５−クロロ−２−ニトロアニリン ３ｇを取り、撹拌しながら温度１８５℃で反応を行った。２０時間反応を行い、液クロで反応液を分析したところ５−イミダゾール−１−イル−２−ニトロアニリンが６５．５％、未反応の５−クロロ−２−ニトロアニリンが３２％であった。
【００１５】
【発明の効果】
従来法に比べ、好収率でしかも副生物の生成を抑制出来ることから反応粗生物の洗浄が簡便で効率良く５−イミダゾール−１−イル−２−ニトロアニリンを得ることが可能になった。[0001]
[Industrial application fields]
The present invention relates to an intermediate 5-imidazol-1-yl- for 6- (1-H-imidazol-1-yl) -7-nitro-2,3- (1H, 4H) -quinoxalinedione having pharmacological action. The present invention relates to a method for producing 2-nitroaniline.
[0002]
[Prior art]
5-Imidazol-1-yl-2-nitroaniline is 6- (1-H-imidazol-1-yl) -7-nitro-2,3- (described in WO 92/07847, which is known as a brain function improving agent. 1H, 4H) -Quinoxalinedione is an important intermediate. Regarding the synthesis method of 5-imidazol-1-yl-2-nitroaniline, JP-A-3-14579 and Journal of Medicinal Chemistry, 1992, Vol. 35, 4455-4463, using an excess amount of imidazole, N , N-dimethylformamide is used as a reaction solvent, or a production method by heating in the absence of a solvent is described.
[0003]
[Problems to be solved by the invention]
According to the conventional method, in order to carry out the reaction in the absence of solvent, imidazole is used in an amount of 6 molar equivalents or more, and a high reaction temperature of about 180 ° C. is required. Although the boiling point of imidazole is 257 ° C. (760 mmHg), it has a sublimation property, and such a method has a problem that the charging efficiency is lowered and the apparatus is blocked. Further, when N, N-dimethylformamide is used as a solvent, there are many by-products and there is a problem that the yield is low.
[0004]
[Means for Solving the Problems]
As a result of intensive studies to find a simple method for producing 5-imidazol-1-yl-2-nitroaniline, the present inventors have reached the present invention. That is, the present invention
(1) A process for producing 5-imidazol-1-yl-2-nitroaniline, which comprises reacting imidazole and 5-halogeno-2-nitroaniline in an aprotic polar solvent having a heterocycle (2 ) The production method according to item (1), wherein imidazole and 5-halogeno-2-nitroaniline are reacted at a molar ratio of 1: 1 to 10 (3) The aprotic polar solvent having a heterocycle is N-methyl-2 -Pyrrolidone, 1,3-dimethyl-2-imidazolidinone, the production method according to item (1), wherein the amount of the aprotic polar solvent having a heterocycle is 1 of 5-halogeno-2-nitroaniline The production method according to (1), which is ˜30 times by weight (5) The production method according to (1), wherein the reaction temperature is 100 to 210 ° C. (6) Imidazole and 5-halogeno-2-nitro The production method according to item (1) wherein the reaction with niline is carried out in the presence of a base (7) The amount of the base used is 0.1 to 5 molar equivalents relative to the molar amount of 5-halogeno-2-nitroaniline. The production method according to item (6).
[0005]
Examples of the 5-halogeno-2-nitroaniline used in the present invention include 5-fluoro-2-nitroaniline, 5-chloro-2-nitroaniline, 5-bromo-2-nitroaniline, 5-iodo-2- Nitroaniline is mentioned. The solvent used is preferably an N-methyl-2-pyrrolidone or 1,3-dimethyl-2-imidazolidinone as an aprotic polar solvent having a heterocycle. It can also be used as a mixed solvent of two types. The amount of the solvent used is 1 to 30 times by weight, preferably 2 to 10 times by weight of 5-halogeno-2-nitroaniline as a substrate. In order to carry out the method of the present invention, imidazole is dissolved in a predetermined solvent in an amount of 1 to 10 molar equivalents of the molar amount of 5-halogeno-2-nitroaniline, and a predetermined amount of 5-halogeno-2-nitroaniline is added while stirring. Then, the temperature in the reaction system is preferably gradually raised to 100 to 210 ° C. by heating, and more preferably stirred at 150 to 200 ° C. for about 5 to 15 hours.
[0006]
Since it takes a long time to complete the reaction under the above reaction conditions, a base such as caustic soda, caustic potash, sodium carbonate, potassium carbonate, sodium bicarbonate is added in an amount of 0.1 to 5 molar equivalents relative to 5-halogeno-2-nitroaniline. The reaction can be completed in a short time by adding 0.2 to 3 molar equivalents.
[0007]
After completion of the reaction, 5-imidazol-1-yl-2-nitroaniline is precipitated by injecting the reaction solution into water 3 to 15 times by weight of the solvent used, and recovered from the reaction system, washed well with water, filtered, A product with high purity can be obtained by drying.
[0008]
In this way, the target product, 5-imidazol-1-yl-2-nitroaniline, can be obtained in good yield and high purity. According to this method, sublimation of imidazole can be suppressed, heating can be performed at a high temperature, and production can be efficiently performed in a short time while suppressing generation of by-products.
Purity can be easily measured by liquid chromatography.
[0009]
【Example】
Hereinafter, the present invention will be described in more detail with reference to examples.
[0010]
Example 1
In a 50 ml glass four-necked flask, 20 g of N-methyl-2-pyrrolidone, 4.0 g of imidazole, 5.0 g of 5-chloro-2-nitroaniline and 1.8 g of sodium carbonate are taken, and the temperature is 180 ° C. with stirring. The reaction was carried out. The reaction was performed for 6 hours, and the reaction solution was analyzed by liquid chromatography. As a result, it was confirmed that the starting material 5-chloro-2-nitroaniline was completely consumed. When the reaction solution was poured into 100 cc of water, 5-imidazol-1-yl-2-nitroaniline was precipitated as an insoluble matter. By filtration, 5.02 g of 5-imidazol-1-yl-2-nitroaniline as a crude product was obtained with a yield of 85% and a liquid chromatographic purity of 95.5%.
The analysis conditions for liquid chromatography are shown below.
Acetonitrile: 0.5% potassium dihydrogen phosphate = 400: 600
Flow rate 1.0 ml / min. Column temperature 40 ° C
[0011]
Example 2
In a 100 ml glass four-necked flask, take 40 g of 1,3-dimethyl-2-imidazolidinone, 20.4 g of imidazole, 34.6 g of 5-chloro-2-nitroaniline, and 16.6 g of potassium carbonate, and stir. The reaction was conducted at a temperature of 180 ° C. The reaction was conducted for 7 hours, and the reaction solution was analyzed by liquid chromatography. As a result, it was confirmed that the starting material 5-chloro-2-nitroaniline was completely consumed. Thereafter, when the reaction solution was poured into 120 cc of water, 5-imidazol-1-yl-2-nitroaniline was precipitated as an insoluble matter. By filtration, 32.6 g of 5-imidazol-1-yl-2-nitroaniline as a crude product was obtained in a yield of 80% and a liquid chromatographic purity of 97.3%.
[0012]
Example 3
In a 50 ml glass four-necked flask, 20 g of N-methyl-2-pyrrolidone, 4.0 g of imidazole, and 5.0 g of 5-chloro-2-nitroaniline were taken and reacted at a temperature of 180 ° C. while stirring. The reaction was conducted for 6 hours, and the reaction mixture was analyzed by liquid chromatography. As a result, 5-imidazol-1-yl-2-nitroaniline was 58.5%, and unreacted 5-chloro-2-nitroaniline was 35.3%. there were.
[0013]
Comparative Example 1
In a 100 ml glass four-necked flask, 60 ml of N, N-dimethylformamide, 27.2 g of imidazole, and 17.3 g of 5-chloro-2-nitroaniline were taken and reacted at a temperature of 165 ° C. with stirring. The reaction was carried out for 8 hours, and the reaction mixture was analyzed by liquid chromatography. As a result, 38.5% of 5-imidazol-1-yl-2-nitroaniline and 40% of unreacted 5-chloro-2-nitroaniline were accompanied by by-products. 0.5% and 20% by-product.
[0014]
Comparative Example 2
A 50 ml glass four-necked flask was charged with 10 g of imidazole and 3 g of 5-chloro-2-nitroaniline, and reacted at a temperature of 185 ° C. with stirring. The reaction was carried out for 20 hours, and the reaction mixture was analyzed by liquid chromatography. As a result, 5-imidazol-1-yl-2-nitroaniline was found to be 65.5% and unreacted 5-chloro-2-nitroaniline was found to be 32%. .
[0015]
【The invention's effect】
Compared with the conventional method, it is possible to obtain 5-imidazol-1-yl-2-nitroaniline easily and efficiently by washing the reaction crude product because the production of by-products can be suppressed with a good yield.
Claims (7)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22909994A JP3698326B2 (en) | 1994-08-31 | 1994-08-31 | Process for producing 5-imidazol-1-yl-2-nitroaniline |
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| JP22909994A JP3698326B2 (en) | 1994-08-31 | 1994-08-31 | Process for producing 5-imidazol-1-yl-2-nitroaniline |
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| Publication Number | Publication Date |
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| JPH0867673A JPH0867673A (en) | 1996-03-12 |
| JP3698326B2 true JP3698326B2 (en) | 2005-09-21 |
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