JPS6317851A - Production of high-purity 3-nitrobenzaldehyde - Google Patents
Production of high-purity 3-nitrobenzaldehydeInfo
- Publication number
- JPS6317851A JPS6317851A JP16323086A JP16323086A JPS6317851A JP S6317851 A JPS6317851 A JP S6317851A JP 16323086 A JP16323086 A JP 16323086A JP 16323086 A JP16323086 A JP 16323086A JP S6317851 A JPS6317851 A JP S6317851A
- Authority
- JP
- Japan
- Prior art keywords
- nitrobenzaldehyde
- benzylideneamine
- formula
- purity
- mol
- 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
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 20
- AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical compound N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 claims abstract description 12
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000003141 primary amines Chemical class 0.000 claims abstract description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000000802 nitrating effect Effects 0.000 claims abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 10
- 150000003973 alkyl amines Chemical class 0.000 claims 3
- 125000003916 ethylene diamine group Chemical group 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 238000007796 conventional method Methods 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 125000005263 alkylenediamine group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- IIVYBNBDIDWPQV-UHFFFAOYSA-N n-ethyl-1-phenylmethanimine Chemical compound CCN=CC1=CC=CC=C1 IIVYBNBDIDWPQV-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QBAKBJNOARBSGP-UHFFFAOYSA-N n-[2-(benzylideneamino)ethyl]-1-phenylmethanimine Chemical compound C=1C=CC=CC=1C=NCCN=CC1=CC=CC=C1 QBAKBJNOARBSGP-UHFFFAOYSA-N 0.000 description 2
- HXTGGPKOEKKUQO-UHFFFAOYSA-N n-methyl-1-phenylmethanimine Chemical compound CN=CC1=CC=CC=C1 HXTGGPKOEKKUQO-UHFFFAOYSA-N 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- -1 ophthylamine Chemical compound 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DXMKVWHXWJBSRG-UHFFFAOYSA-N (3-nitrophenyl)methanimine Chemical compound [O-][N+](=O)C1=CC=CC(C=N)=C1 DXMKVWHXWJBSRG-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- JMPRVUAYOASENX-UHFFFAOYSA-N 4-phenylbuta-1,2,3-trienylbenzene Chemical group C=1C=CC=CC=1C=C=C=CC1=CC=CC=C1 JMPRVUAYOASENX-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- LWHMWTVYYKNHQA-UHFFFAOYSA-N pentane-1,2,5-triamine Chemical compound NCCCC(N)CN LWHMWTVYYKNHQA-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、高純度３−ニトロベンズアルデヒドの製造法
に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for producing high purity 3-nitrobenzaldehyde.
該化合物は、医薬、特に降圧剤等の中間原料として有用
でおり、その他、幅広い用途が考えられる重要な化合物
である。This compound is useful as an intermediate raw material for medicines, especially antihypertensive agents, and is an important compound that can be used in a wide range of other applications.
（従来の技術）（発明が解決しようとする問題点）
従来、３−ニトロベンズアルデヒドを・要）ｈする方法
としては、通常、オーカニツク シンセシス （０ＲＧ
ＡＮＩＣ，ＳＹ＼−ＴＨＥＳＩｓ＞第３巻６４４頁に記
載されているように、ベンズアルデヒドを直接ニトロ化
する方法が示されているが、この反応では下記の如く、
目的とする３−ニトロベンズアルデじドの他に異性体で
ある２−ニトロベンズアルデヒドが約２０％生成する。(Prior Art) (Problems to be Solved by the Invention) Conventionally, as a method for producing 3-nitrobenzaldehyde, organic synthesis (0RG) is usually used.
As described in ANIC, SY\-THESIs>Vol. 3, page 644, a method for directly nitrating benzaldehyde is shown, but in this reaction, as follows:
In addition to the desired 3-nitrobenzaldehyde, about 20% of the isomer 2-nitrobenzaldehyde is produced.
したがって、高純度３−ニトロベンズアルデヒドを取得
する場合、３−ニトロベンズアルデヒドと２−二トロベ
ンズアルデヒドの混合物から異性体を分離するための特
別な精製工程が必要となる。Therefore, when obtaining high purity 3-nitrobenzaldehyde, a special purification step is required to separate the isomers from the mixture of 3-nitrobenzaldehyde and 2-nitrobenzaldehyde.
オーガニック シンセシスでは、２−二トロ化物と３−
二トロ化物を蒸密により分離しているが、本文にも記載
されているように爆発の危険性があり、また収率面でも
満足できるものではない。In organic synthesis, 2-nitro compound and 3-
Nitroide is separated by steaming, but as mentioned in the text, there is a risk of explosion and the yield is not satisfactory.
また西ドイツ公開特許第３２１２０６９号公報では、２
−二トロ化物と３−二トロ化物をアセタール化したのち
、蒸沼により分離する手Ｖをとっているが１．精製法と
しては複雑であり、また上記オーガニック シンセシス
の場合と同様に収率面で満足すべきものではない。Furthermore, in West German Published Patent No. 3212069, 2
- After acetalizing the -nitroide and the 3-nitroide, we are taking steps to separate them using a steam swamp, but 1. As a purification method, it is complicated, and as with the organic synthesis described above, it is not satisfactory in terms of yield.
この他、行間溶媒、たとえばアルコールによる再結晶、
また−度、亜硫酸水素ナトリウム付加物にしたの５２−
二トロ化物と３−二トロ化物の溶解度差を利用した分離
等の手段もあるが、決して完全なものではなく、しかも
収率面でも満足すべきものではない。In addition, recrystallization with interline solvents such as alcohol,
Also, 52- degrees of sodium hydrogen sulfite adduct
Although there are separation methods that utilize the difference in solubility between nitronide and 3-nitronide, they are by no means perfect and are not satisfactory in terms of yield.
本発明者らは、前記欠点を排除して工業的に安価に、そ
して容易に該化合物を製造する方法について鋭意検討し
た結果、ベンジリデンアミンをニトロ化すると選択的に
３位がニトロ化され、２−ニトロ化物は生成しないこと
を児い出し本発明に至った。The present inventors have conducted intensive studies on a method for manufacturing the compound industrially at low cost and easily by eliminating the above-mentioned drawbacks. As a result, when benzylideneamine is nitrated, the 3-position is selectively nitrated, and the 2-position is selectively nitrated. -We have discovered that nitrated compounds are not produced, leading to the present invention.
（問題点を解決するための手段）
本発明の要旨は下式に示すようにベンジリデンアミンを
ニトロ化、引ぎ続ぎ加水分解することを特徴とする高純
度３−ニトロベンズアルデヒドの製造法である。(Means for Solving the Problems) The gist of the present invention is a method for producing high-purity 3-nitrobenzaldehyde, which is characterized by nitration of benzylidene amine and subsequent hydrolysis as shown in the following formula. .
（ここにＲはアルキル基、アリール基を示す）
すなわち、公知の如くベンジリデンアミンはベンズアル
デヒドと第一級アミンから定量的に生成するが、このも
のをニトロ化すると３位が選択的にニトロ化され、２位
は全くニトロ化されないことを見い出し本発明に至った
。生成した３−ニトロベンジリデンアミンは酸で容易に
加水分＠され、定量的に３−二トロベンズアルデヒドと
なり、当然、異性体等は存在しないため、特別な精製工
程は不必要となり、また収率も大幅に向上することから
、３−二トロベンズアルデヒドの”ｌＪ３’Ａ法として
は画期的といえる。(Here, R represents an alkyl group or an aryl group.) In other words, as is known, benzylidene amine is quantitatively produced from benzaldehyde and a primary amine, but when this product is nitrated, the 3-position is selectively nitrated. It was discovered that the second position was not nitrated at all, leading to the present invention. The generated 3-nitrobenzylideneamine is easily hydrolyzed with acid and quantitatively becomes 3-nitrobenzaldehyde. Naturally, there are no isomers, so a special purification process is unnecessary and the yield is also low. Since the improvement is significant, it can be said that the "lJ3'A method" for 3-nitrobenzaldehyde is revolutionary.
原料のベンジリデンアミンは、市販のものをそのまま使
用することもできるが、ベンズアルデヒドと第一級アミ
ンとの反応により１７られるベンジリデンアミンを用い
てもよい。As the raw material benzylidene amine, a commercially available one can be used as is, but a benzylidene amine prepared by reacting benzaldehyde with a primary amine may also be used.
その場合、使用する第一級アミンとしては、メチルアミ
ン、エチルアミン、プロピルアミン、ｎ−ブチルアミン
等の低級アミン類、エチレンジアミン、プロピレンジア
ミン等のアルキレンジアミン類、ジエチレントリアミン
。In this case, the primary amines used include lower amines such as methylamine, ethylamine, propylamine, and n-butylamine, alkylene diamines such as ethylenediamine and propylene diamine, and diethylenetriamine.
トリエチレンテトラミン、トリアミンプロパン、 １，
２．３−トリアミノペンタン、 １，２．５−トリアミ
ノペンタン等のポリアミン類ヘキシルアミン、オフチル
アミン、ドデシルアミン等の高級アミン類、Ｐ−ニトロ
アニリン、０−二トロアニリン等の芳香酸アミン類等が
必る。Triethylenetetramine, triamine propane, 1,
Polyamines such as 2.3-triaminopentane and 1,2.5-triaminopentane, higher amines such as hexylamine, ophthylamine, and dodecylamine, aromatic acid amines such as P-nitroaniline and 0-nitroaniline, etc. is necessary.
特に、エチレンジアミン等のアルキレンジアミン類は、
ベンズアルデヒド２分子と反応し、ジベンジリデンアル
キレンジアミンとなるため、高純度３−ニトロベンズア
ルデヒドの製造法としては経済的であるため好適に用い
られる。In particular, alkylene diamines such as ethylene diamine,
Since it reacts with two molecules of benzaldehyde to form dibenzylidene alkylene diamine, it is economical and is therefore preferably used as a method for producing high purity 3-nitrobenzaldehyde.
また、使用したアミンを回収して再使用する場合には、
水に難溶性の高級アミンを使用すれば回収が可能となり
有利である。In addition, when recovering and reusing used amines,
It is advantageous to use higher amines that are poorly soluble in water because they can be recovered.
このようにして得られたベンジリデンアミンは、公知の
方法でニトロ化、加水分解の操作を経て３−ニトロベン
ズアルデヒドとなる。The benzylidene amine thus obtained is converted into 3-nitrobenzaldehyde through nitration and hydrolysis operations using known methods.
（実施例）
次に実施例により、本発明の詳細な説明するが、本発明
はこれら実施例のみに限定されるものではない。(Examples) Next, the present invention will be explained in detail with reference to Examples, but the present invention is not limited to these Examples.
実施例−１
攪拌器１滴下ロート、温度計及び冷却器を備えた１ｇ容
量４つロフラスコに９８％硫酸６７５９ （６，７５モ
ル）を仕込み、１０℃にてベンジリデンメチルアミン６
１９．０７ （１，０モル）を１時間を要して滴下し、
ざらに５℃にて９５９６発煙硝酸６９．６９（１，０５
モル）を１時間を要して滴下し、さらに同温度で２時間
攪拌した。その後、反応液を水中に添加し、生成物をク
ロロホルムで抽出し、クロロホルムを留去することによ
り残留物１４６．５ｇを得た。Example-1 98% sulfuric acid 6759 (6.75 mol) was charged into four 1g capacity flasks equipped with a stirrer, a dropping funnel, a thermometer, and a condenser, and benzylidene methylamine 6 was added at 10°C.
19.07 (1.0 mol) was added dropwise over 1 hour,
9596 fuming nitric acid 69.69 (1,05
mol) was added dropwise over a period of 1 hour, and the mixture was further stirred at the same temperature for 2 hours. Thereafter, the reaction solution was added to water, the product was extracted with chloroform, and the chloroform was distilled off to obtain 146.5 g of a residue.
これをイソプロパツールで再結晶することにより、淡黄
白色結晶の３−二トロベンズアルデヒド１３５．５ｇ（
融点５７−５８℃）を得た。By recrystallizing this with isopropanol, 135.5 g of 3-nitrobenzaldehyde (
melting point 57-58°C).
ガスクロマトグラフィーによる純度は１００％であった
。Purity by gas chromatography was 100%.
ベンジリデンメチルアミンに対する収率は、８９．７％
であった。Yield based on benzylidene methylamine is 89.7%
Met.
実施例−２
攪拌器２滴下ロート、温度計及び冷却器を備えた１ｇ容
量４つロフラスコにベンズアルデヒド２１２．０ｇ（２
，０モル）を仕込み、４５−５５°Ｃにてエチレンジア
ミン６６．０９ （１，１モル）を１時間を要して滴下
し、ざらに同温度にて、１時間攪拌した。Example-2 212.0 g of benzaldehyde (2
, 0 mol) was added thereto, and 66.09 (1.1 mol) of ethylenediamine was added dropwise at 45-55°C over a period of 1 hour, and the mixture was roughly stirred at the same temperature for 1 hour.
その後、水８００ ｇを添加し、攪拌下に２０’Ｃまで
冷却し、析出した結晶を 過、水洗、乾燥することによ
り、白色結晶のジベンジリデンエチレンジアミン２２９
．０９を得た。引きつづき攪拌器９滴下ロート、温度計
及び冷却器を備えた１ｆ１容量４つロフラスコに９８％
硫酸６７５ ｇ（６，７５モル）を仕込み、１０℃にて
ジベンジリデンエチレンジアミン１１８．０３（０，５
モル）を１時間を要して滴下し、ざらに５℃にて９５％
発煙硝酸６９．６ ｇ（１，０５モル）を１時間を要し
て滴下し、ざらに同温度で２時間攪拌した。その俊、反
応液を水中に添加し、生成物をクロロホルムで抽出し、
クロロホルムを留去することにより、残留物１５１．１
７を得た。これをイソプロパツールで再結晶することに
より、淡黄白色結晶の３−二トロベンズアルデヒド１３
６．０９ （融点５７−５８℃）を１ｑだ。Thereafter, 800 g of water was added, the mixture was cooled to 20'C with stirring, and the precipitated crystals were filtered, washed with water, and dried to obtain white crystals of dibenzylideneethylenediamine 229.
．． I got 09. 98% in a 1f1 capacity 4 flask equipped with a stirrer, 9 dropping funnels, a thermometer and a condenser.
675 g (6.75 mol) of sulfuric acid was charged, and 118.03 (0.5 mol) of dibenzylidene ethylene diamine was added at 10°C.
mol) was added dropwise over 1 hour, and the mixture was heated to 95% at 5°C.
69.6 g (1.05 mol) of fuming nitric acid was added dropwise over 1 hour, and the mixture was roughly stirred at the same temperature for 2 hours. Then, the reaction solution was added to water, the product was extracted with chloroform,
By distilling off the chloroform, a residue of 151.1
I got a 7. By recrystallizing this with isopropanol, pale yellowish white crystals of 3-nitrobenzaldehyde 13 were obtained.
6.09 (melting point 57-58℃) is 1q.
ガスクロマトグラフィーによる純度は１００％であった
。Purity by gas chromatography was 100%.
ジベンジリデンエチレンアミンに対する収率は９０．１
％、ベンズアルデヒドに対する収率は８７゜４％であっ
た。Yield based on dibenzylidene ethylene amine is 90.1
%, the yield based on benzaldehyde was 87.4%.
実施例−３
滑拌器、＠下ロート、温度計及び冷却器を備えた１ｇ容
量４つロフラスコにベンズアルデヒド２１２．０！Ｊ
（２，０モル）を仕込み、１５−２０’Ｃにて３３％エ
チルアミン水溶液４３６．４ ｇ（３，２モル）を１時
間を要して滴下し、さらに同温度にて、１時間攪拌した
。Example-3 212.0 benzaldehyde in four 1g capacity flasks equipped with a slip stirrer, lower funnel, thermometer and condenser! J
(2.0 mol) was added dropwise at 15-20'C over a period of 1 hour with 436.4 g (3.2 mol) of a 33% ethylamine aqueous solution, and the mixture was further stirred at the same temperature for 1 hour. .
その後、分液によりオイル状物２７１．６９をＩＨだ。After that, 271.69% of the oily substance was separated into IH.
このオイル状物を減圧魚雷することにより、ベンジリデ
ンエチルアミン（１１６〜１１８°Ｃ／１２ｍｍｈｌｌ
＞ ２５８．０ｙを得た。By vacuum torpedoing this oily substance, benzylidene ethylamine (116-118°C/12mmHL) was prepared.
>258.0y was obtained.
引きつづき、ベンジリデンエチルアミン１３３．０９
（１，０モル）を用い、実施例−１と全く同様の操作を
行ない、３−ニトロベンズアルデヒド１３５．７’７
（融点５７−５８°Ｃ）を得た。Continuing, benzylidene ethylamine 133.09
(1.0 mol), the same operation as in Example-1 was carried out, and 3-nitrobenzaldehyde 135.7'7
(melting point 57-58°C) was obtained.
ガスクロマトグラフィーによる純度は１００％でめった
。Purity by gas chromatography was 100%.
ベンジリデンエチルアミンに対する収率は８９．９％、
ベンズアルデヒドに対する収率は８７．２％でめった。The yield based on benzylidene ethylamine was 89.9%.
The yield based on benzaldehyde was 87.2%.
（発明の効果）
本発明は、医薬、農薬等の中間体として有用な３−ニト
ロベンズアルデヒドを製造するに際して、ベンジリデン
アミンをニトロ化。(Effects of the Invention) The present invention nitrates benzylideneamine when producing 3-nitrobenzaldehyde, which is useful as an intermediate for medicines, agricultural chemicals, and the like.
加水分解する新規な製造法を提供するものである。The present invention provides a new production method that involves hydrolysis.
本発明の方法によれば、異姓体を含まない高純度の目的
物を収率よく１ユることがてきるので従来技術と比較し
て非常に右利で必り、産業界に寄与するところ大である
。According to the method of the present invention, it is possible to obtain 1 unit of a highly pure target product containing no allomorphs with a good yield, which is very advantageous compared to the conventional technology, and will definitely contribute to the industry. It's large.
Claims (5)
とを特徴とする高純度３−ニトロ ベンズアルデヒドの製造法。(1) A method for producing high-purity 3-nitrobenzaldehyde, which comprises nitrating and hydrolyzing benzylideneamine.
アミンの反応によって得られたも のである特許請求の範囲（１）記載の方法。(2) The method according to claim (1), wherein the benzylidene amine is obtained by reacting benzaldehyde with a primary amine.
範囲（２）記載の方法。(3) The method according to claim (2), wherein the primary amine is an alkylamine.
求の範囲（３）記載の方法。(4) The method according to claim (3), wherein the alkylamine is ethylenediamine.
範囲（３）記載の方法。(5) The method according to claim (3), wherein the alkylamine is methylamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16323086A JPS6317851A (en) | 1986-07-10 | 1986-07-10 | Production of high-purity 3-nitrobenzaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16323086A JPS6317851A (en) | 1986-07-10 | 1986-07-10 | Production of high-purity 3-nitrobenzaldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6317851A true JPS6317851A (en) | 1988-01-25 |
Family
ID=15769798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16323086A Pending JPS6317851A (en) | 1986-07-10 | 1986-07-10 | Production of high-purity 3-nitrobenzaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6317851A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8962521B2 (en) | 2006-04-26 | 2015-02-24 | Kyodo Printing Co., Ltd. | Coating for humidity indicator, method for production of the coating, and humidity indicator using the coating |
-
1986
- 1986-07-10 JP JP16323086A patent/JPS6317851A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8962521B2 (en) | 2006-04-26 | 2015-02-24 | Kyodo Printing Co., Ltd. | Coating for humidity indicator, method for production of the coating, and humidity indicator using the coating |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2268586A1 (en) | Process for producing n-glycyltyrosine and its crystal structure | |
| JPS6317851A (en) | Production of high-purity 3-nitrobenzaldehyde | |
| JPS6155902B2 (en) | ||
| RU2097372C1 (en) | Method of synthesis of aromatic azomethine | |
| US5382689A (en) | Process for preparation of bevantolol hydrochloride | |
| WO2003002517A1 (en) | Process for the preparation of 1.1-cyclohexane diacetic acid monoamide | |
| JPS6150A (en) | Production of n-acylaminoacid amide | |
| US5792880A (en) | Process for the preparation of N-lauroyl-L-glutamic acid di-n-butylamide | |
| US5583256A (en) | Process for producing 1,3-dialkyl-2-imidazolidinone | |
| JPH02196757A (en) | Preparation of 2-chlorobenzylamine | |
| SU289084A1 (en) | METHOD OF OBTAINING L / -METHIL-I - [(p-AROYALAMIDO) -ETHYL] - ANILINES | |
| KR20130134407A (en) | Process for preparing gefitinib and an intermediate used for preparing thereof | |
| JP3486922B2 (en) | Method for producing acid amide | |
| JPS6312465B2 (en) | ||
| CN116606238A (en) | N-Boc-3-nitroindole and preparation method thereof | |
| JPH0446175A (en) | Production of 5-hydroxy-3,4-methylenedioxybenzoic acid derivative | |
| US5514793A (en) | 1,3,6-trialkylhexahydro-1,3,6-triazocine-2-on and preparation process thereof | |
| SU1696426A1 (en) | Method of 2 | |
| CN116621762A (en) | 3-nitroindole analogue and preparation method thereof | |
| KR20230034575A (en) | Process for Preparing Itopride Hydrochloride | |
| SU670563A1 (en) | Method of producing phenoxyalkyl amines | |
| SU465781A3 (en) | Method for producing -diaminoalkanes | |
| JP4521090B2 (en) | Process for producing 1,1,1-trifluoro-2-aminoalkane | |
| JPH08208587A (en) | Purification of n,o-dialkylhydroxamic acid and o-alkylhydroxamic acid | |
| JP2001322981A (en) | Method for producing n,n'-carbonylbislactam |