JP4182271B2 - Method for producing naphthoic acid aryl ester derivative - Google Patents
Method for producing naphthoic acid aryl ester derivative Download PDFInfo
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- JP4182271B2 JP4182271B2 JP03335199A JP3335199A JP4182271B2 JP 4182271 B2 JP4182271 B2 JP 4182271B2 JP 03335199 A JP03335199 A JP 03335199A JP 3335199 A JP3335199 A JP 3335199A JP 4182271 B2 JP4182271 B2 JP 4182271B2
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- 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
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
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Description
【０００１】
【発明の属する技術分野】
本発明は、写真薬、染料、顔料などの合成中間体有用なナフトエ酸アリールエステル誘導体の製造方法に関するものである。
【０００２】
【従来の技術】
多環式オキシカルボン酸アリールエステルの製造法としては、従来、多環式オキシカルボン酸又はその誘導体とフェノール類とを反応させる方法が一般的に知られている。しかし、これら従来の方法は、通常のエステル類合成法である強酸を触媒として使用するため、カルボン酸の分解を伴い、その使用に制限がある。また、反応試剤として、三塩化リン、オキシ塩化リン、五塩化リンなどを使用する方法があるが、これらの公知の方法では概して収率が低く、また製品に着色がみられ、精製工程に手間を要する等のため工業的な方法とは言えない。
【０００３】
本発明の目的とする１−ヒドロキシ−５−置換アミノ−２−ナフトエ酸アリールエステル誘導体は、カラー写真感光材料の分野においてシアン色素形成カプラーの合成中間体として重要な中間体であり、その合成法の開発は重要な課題となっている。
【０００４】
従来、この化合物の製造方法としては、例えば１−ヒドロキシ−５−置換アミノ−２−ナフトエ酸クロライドを塩化アルミニウム触媒の存在下フェノール類と反応させる方法が一般的であるが、収率、純度等において満足できるものではなく、特開昭６３−９３７５４号公報には、５−置換アミノナフトール誘導体と、クロロ蟻酸アリールとからフリーデル・クラフツ反応によって製造する方法が記載されているが、この方法では塩化アルミニウム、塩化鉄、塩化チタンなどを使用するため、それらの取り扱いが難しく、また収率も７０〜７５％程度であって、工業的製造法としては、必ずしも充分とは言えない。
【０００５】
一方、ナフトエ酸アリールエステルを製造する方法としては、例えば特公昭５８−２２０２１号公報、特開昭６４−４５３４１号公報に、反応剤としてトリアリール亜リン酸エステルを用いる方法が提案されているが、これは特殊な化合物についての例であり、これらには、本発明の目的とする１−ヒドロキシ−５−置換アミノ−２−ナフトエ酸アリールエステル誘導体については何等記載がない。
【０００６】
【発明が解決しようとする課題】
本発明の目的は、１−ヒドロキシ−５−置換アミノ−２−ナフトエ酸アリールエステル誘導体を高純度、高収率で工業的に製造する方法を提供することである。
【０００７】
【課題を解決するための手段】
本発明の方法は、一般式（１）
【化１】
（式中、Ｒ１は更に置換されていてもよいアルキル基、Ｒ２は水素原子、アルキル基又はハロゲン原子を表す。）
で示されるナフトエ酸誘導体と、一般式（２）
【化２】
（式中、Ｒ３は水素原子、アルキル基又はハロゲン原子を表わし、ｎは０〜３の整数を表わす。但し、ｎが２以上の場合、Ｒ３は同じであっても異なっていてもよい。）
で示されるトリアリール亜リン酸エステルとを、反応溶媒の存在又は不存在下に反応させることを特徴とする一般式（３）
【化３】
（式中、Ｒ１、Ｒ２及びＲ３はそれぞれ前記の意味を有する。）
で示されるナフトエ酸アリールエステル誘導体の製造方法である。
【０００８】
【発明の実施の形態】
以下、本発明の方法を詳しく説明する。
一般式（１）及び（２）におけるＲ１で示される更に置換されていてもよいアルキル基の具体例としては、メチル、エチル、ｎ−プロピル、ｉ−プロピル、ｎ−ブチル、ｉ−ブチル、シクロヘキシル、１−エチルペンチル、２−エチルヘキシル、ベンジル、トリフルオロメチル、クロロメチルなどの炭素数１〜２０のアルキル基が挙げられる。
また、一般式（１）、（２）及び（３）におけるＲ２及びＲ３で示されるアルキル基の具体例としては、それぞれ独立にメチル、エチル、ｎ−プロピル、ｉ−プロピル、ｎ−ブチル、ｉ−ブチル、シクロヘキシル、１−エチルペンチル、２−エチルヘキシル等が挙げられる。
【０００９】
本発明の特徴は、前記一般式（３）で示される１−ヒドロキシ−５−置換アミノ−２−ナフトエ酸アリールエステル誘導体を工業的有利に製造するために、反応試剤としてトリアリール亜リン酸エステルを用いることにある。
本発明に用いる一般式（２）で示されるトリアリール亜リン酸エステルは、前記特公昭５８−２２０２１号公報又は特開昭６４−５３４１号公報に記載されるものを用いることができる。具体的には例えば三塩化リン１モルに対し少なくとも３モルのフェノール類を反応せしめて得られるトリアリール亜リン酸エステル類が好ましく用いられ、ここでフェノール類としては、フェノール、ハロゲン化フェノール類、アルキルフェノール類（アルキル基は前記の意味を有する）が挙げられる。
【００１０】
この一般式（２）で示されるトリアリール亜リン酸エステル類の使用量は、一般式（１）で示されるナフトエ酸誘導体に対して、反応性を促進するため０．８モル比以上、特に好ましくは１．０〜１．５モル比の範囲で使用される。さらに過剰の使用は不経済である。
【００１１】
反応温度は、１８０℃以下、特に好ましくは８０℃〜１３０℃の範囲である。１８０℃以上では不純物が多く生成し、８０℃以下の場合は反応速度が著しく遅くなる。
【００１２】
本発明の方法は、反応溶媒を用いることにより、更に有利に目的とするナフトエ酸アリールエステル誘導体を製造することができる。ここで、用いることのできる反応溶媒の具体例としては、フェノール、ハロゲン化フェノール、アルキルフェノール（クレゾール）等のフェノール類、トルエン、キシレン等の芳香族炭化水素類、モノ−、ジ−若しくはトリクロロベンゼン等のハロゲン化炭化水素類、メチル−ｎ−プロピルケトン、メチル−ｎ−ブチルケトン、メチル−ｎ−イソブチルケトン、ジイソブチルケトン等の脂肪族ケトン類、ジメチルホルムアミド、ジメチルアセトアミド等の酸アミド類が例示される。これらの中でもフェノール類が特に好ましく用いられる。
溶媒の使用量としては、一般式（１）で示されるナフトエ酸誘導体に対して、０．５から６倍量で使用される。
【００１４】
本発明の方法によれば、カルボン酸の分解による副生成物の生成が少なく、高純度、高収率で目的とする１−ヒドロキシ−５−置換アミノ−２−ナフトエ酸アリールエステル誘導体を工業的に有利に製造することができる。
【００１５】
【実施例】
次に、本発明を実施例に基づいてさらに詳細に説明するが、本発明はかかる実施例のみに限定されるものではない。
【００１６】
実施例１
攪拌機付き容量２１の反応器に、トリフェニルホスフアイト（以下、ＴＰＰと称す）１２８ｇとフェノール８９ｇ、５−イソブトキシカルボニルアミノ−１−ヒドロキシ−２−ナフトエ酸（以下、５ＢＣと称す）１０７ｇ（ＴＰＰ／５ＢＣモル比１．１７モル比）を仕込み、１１５℃まで加熱昇温し、この温度で４時間反応を行った。
内容物は黒褐色透明の液状となり、反応は完結した。この間、液体クロマトグラフにより末反応５ＢＣの分析を実施し、反応終点を判定した。
次いで、内容物に６３０ｇのメタノール水（メタノール濃度９０重量％）を滴下し、さらに６１０ｍｌの水を滴下した。室温まで冷却後析出物を濾別し、更に温水洗浄後乾燥して、目的とする５−イソブトキシカルボニルアミノ−１−ヒドロキシ−２−ナフトエ酸フェニルエステル１２６ｇを得た。収率は９３．８％であった。このものの融点は１５０〜１５１℃で、液体クロマトグラフによる組成分析の結果、純度は９９．４％であった。
【００１９】
実施例４
５ＢＣ１０７ｇに対し、ＴＰＰ１２８ｇ及び溶媒としてトルエン５００ｍｌを加え、実施例１と同様に反応を行なった。内容物を水１０００ｍｌに滴下し水蒸気蒸留によりトルエンを留去した。室温まで冷却後、析出物を濾別し、水洗後乾燥して目的とする５−イソブトキシカルボニルアミノ−１−ヒドロキシ−２−ナフトエ酸フェニルエステル１２７ｇ（収率９４．９％）を得た。このものの液体クロマトグラフによる組成分析の結果、純度は９７．３％であった。
【００２０】
実施例５
５ＢＣ１０７ｇに対し、ＴＰＰ１２８ｇとフェノール８９ｇを仕込み、１３０℃まで加熱昇温し、この温度で４時間反応を行なった。実施例１と同様の取り出し法により目的とする５−イソブトキシカルボニルアミノ−１−ヒドロキシ−２−ナフトエ酸フェニルエステル１１６ｇ（収率８６．３％）を得た。このものの液体クロマトグラフによる組成分析の結果、純度は９８．６％であった。
【００２１】
比較例１
５ＢＣ１０７ｇとフェノール３６．５ｇ及びジメチルホルムアミド３００ｇを仕込み、温度７０〜８０℃で塩化チオニル５０．４ｇを滴下し、この温度で２時間反応を行なった。
内容物を水１０００ｍｌに滴下し、析出物を濾別し、さらに水洗後乾燥した。目的とする５−イソブトキシカルボニルアミノ−１−ヒドロキシ−２−ナフトエ酸フェニルエステル９４ｇ（収率７０．２％）を得た。このものの液体クロマトグラフによる組成分析の結果、純度は９６．８％であった。
【００２２】
実施例６
攪拌機付き容量２１の反応器に、トリ（４−メチルフェニル）ホスファイト１８６ｇとパラクレゾール１００ｇ、８−ブロム−５−イソブトキシカルボニルアミノ−１−ヒドロキシ−２−ナフトエ酸１３５ｇを仕込み、１２０℃まで加熱昇温し、この温度で４時間反応を行なった。内容物は黒褐色透明の液体となり、反応は完結した。反応終点を液体クロマトで確認後、内容物に９００ｇのメタノール水（メタノール濃度９０重量％）を滴下し、室温まで冷却した。析出物を濾別し、さらに水洗後乾燥し、目的とする８−ブロム−５−イソブトキシカルボニルアミノ−１−ヒドロキシ−２−ナフトエ酸（４’−メチルフェニル）エステル１３０ｇ（収率７７．９％）を得た。このものの液体クロマトグラフによる組成分析の結果、純度は９５．２％であった。
【００２３】
実施例７
ＴＰＰ１２８ｇとフェノール８９ｇ、５−イソブトキシカルボニルアミノ−７−ｔブチル−１−ヒドロキシ−２−ナフトエ酸１２７．２ｇを仕込み、１１５℃まで加熱昇温し、この温度で４時間反応を行なった。内容物は黒褐色透明の液体となり、反応は完結した。反応終点を液体クロマトで確認後、内容物に６３０ｇのメタノール水（メタノール濃度９０重量％）を滴下し、更に６１０ｍｌの水を滴下した。室温まで冷却後析出物を濾別し、さらに温水洗後乾燥して、目的とする５−イソブトキシカルボニルアミノ−７−ｔブチル−１−ヒドロキシ−２−ナフトエ酸フェニルエステル１４３ｇ（収率９２．８％）を得た。このものの液体クロマトグラフによる組成分析の結果、純度は９９．０％であった。
【００２４】
【発明の効果】
本発明によれば、写真薬、染料、顔料の合成中間体として有用なナフトエ酸アリール誘導体が高純度、高収率で工業的有利に製造することができるという、効果が奏される。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a process for producing a naphthoic acid aryl ester derivative useful as a synthetic intermediate for photographic drugs, dyes, pigments and the like.
[0002]
[Prior art]
As a method for producing a polycyclic oxycarboxylic acid aryl ester, a method of reacting a polycyclic oxycarboxylic acid or a derivative thereof with a phenol is generally known. However, since these conventional methods use a strong acid, which is a usual ester synthesis method, as a catalyst, they involve decomposition of the carboxylic acid and have limited use. In addition, there are methods using phosphorous trichloride, phosphorous oxychloride, phosphorous pentachloride, etc. as reaction reagents, but these known methods generally have low yields, and the product is colored, which makes the purification process laborious. Therefore, it is not an industrial method.
[0003]
The 1-hydroxy-5-substituted amino-2-naphthoic acid aryl ester derivative which is an object of the present invention is an important intermediate as a synthesis intermediate of a cyan dye-forming coupler in the field of color photographic light-sensitive materials. Development has become an important issue.
[0004]
Conventionally, as a method for producing this compound, for example, a method in which 1-hydroxy-5-substituted amino-2-naphthoic acid chloride is reacted with phenols in the presence of an aluminum chloride catalyst is generally used. In JP-A-63-93754, there is described a process for producing a 5-substituted aminonaphthol derivative and an aryl chloroformate by Friedel-Crafts reaction. Since aluminum chloride, iron chloride, titanium chloride and the like are used, they are difficult to handle, and the yield is about 70 to 75%, which is not necessarily sufficient as an industrial production method.
[0005]
On the other hand, as a method for producing an aryl ester of naphthoic acid, for example, Japanese Patent Publication No. 58-22021 and Japanese Patent Application Laid-Open No. 64-45341 propose a method using triaryl phosphite as a reactant. This is an example of a special compound, and they do not describe anything about the 1-hydroxy-5-substituted amino-2-naphthoic acid aryl ester derivatives that are the object of the present invention.
[0006]
[Problems to be solved by the invention]
An object of the present invention is to provide a method for industrially producing a 1-hydroxy-5-substituted amino-2-naphthoic acid aryl ester derivative with high purity and high yield.
[0007]
[Means for Solving the Problems]
The method of the present invention is represented by the general formula (1)
[Chemical 1]
(In the formula, R 1 represents an optionally substituted alkyl group, and R 2 represents a hydrogen atom, an alkyl group, or a halogen atom.)
A naphthoic acid derivative represented by the general formula (2)
[Chemical formula 2]
(In the formula, R 3 represents a hydrogen atom, an alkyl group or a halogen atom, and n represents an integer of 0 to 3. However, when n is 2 or more, R 3 may be the same or different. .)
And a triaryl phosphite represented by the general formula (3), which is reacted in the presence or absence of a reaction solvent.
[Chemical 3]
(Wherein R 1 , R 2 and R 3 each have the above-mentioned meaning)
It is a manufacturing method of the naphthoic acid aryl ester derivative shown by these.
[0008]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the method of the present invention will be described in detail.
Specific examples of the optionally substituted alkyl group represented by R 1 in the general formulas (1) and (2) include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, Examples thereof include alkyl groups having 1 to 20 carbon atoms such as cyclohexyl, 1-ethylpentyl, 2-ethylhexyl, benzyl, trifluoromethyl, chloromethyl and the like.
Specific examples of the alkyl group represented by R 2 and R 3 in the general formulas (1), (2) and (3) are each independently methyl, ethyl, n-propyl, i-propyl, n-butyl. I-butyl, cyclohexyl, 1-ethylpentyl, 2-ethylhexyl and the like.
[0009]
A feature of the present invention is that a triaryl phosphite ester is used as a reaction reagent in order to produce the 1-hydroxy-5-substituted amino-2-naphthoic acid aryl ester derivative represented by the general formula (3) industrially advantageously. Is to use.
As the triaryl phosphite represented by the general formula (2) used in the present invention, those described in JP-B-58-22021 or JP-A-64-5341 can be used. Specifically, for example, triaryl phosphites obtained by reacting at least 3 moles of phenol with 1 mole of phosphorus trichloride are preferably used. Examples of the phenols include phenol, halogenated phenols, Examples include alkylphenols (the alkyl group has the above-mentioned meaning).
[0010]
The use amount of the triaryl phosphite represented by the general formula (2) is 0.8 mole ratio or more, particularly in order to promote the reactivity with respect to the naphthoic acid derivative represented by the general formula (1). Preferably it is used in the range of 1.0 to 1.5 molar ratio. Furthermore, excessive use is uneconomical.
[0011]
The reaction temperature is 180 ° C. or lower, particularly preferably in the range of 80 ° C. to 130 ° C. When the temperature is 180 ° C. or higher, many impurities are generated. When the temperature is 80 ° C. or lower, the reaction rate is remarkably slow.
[0012]
In the method of the present invention, the target naphthoic acid aryl ester derivative can be more advantageously produced by using a reaction solvent. Here, specific examples of the reaction solvent that can be used include phenols such as phenol, halogenated phenol, and alkylphenol (cresol), aromatic hydrocarbons such as toluene and xylene, mono-, di-, and trichlorobenzene. And halogenated hydrocarbons, methyl-n-propyl ketone, methyl-n-butyl ketone, aliphatic ketones such as methyl-n-isobutyl ketone and diisobutyl ketone, and acid amides such as dimethylformamide and dimethylacetamide . Of these, phenols are particularly preferably used.
The amount of the solvent used is 0.5 to 6 times the amount of the naphthoic acid derivative represented by the general formula (1).
[0014]
According to the method of the present invention, the desired 1-hydroxy-5-substituted amino-2-naphthoic acid aryl ester derivative is industrially produced in a high purity and high yield with little by-product formation due to decomposition of the carboxylic acid. Can be advantageously produced.
[0015]
【Example】
Next, the present invention will be described in more detail based on examples, but the present invention is not limited to such examples.
[0016]
Example 1
A reactor having a capacity of 21 with a stirrer was charged with 128 g of triphenyl phosphite (hereinafter referred to as TPP) and 89 g of phenol, 107 g of 5-isobutoxycarbonylamino-1-hydroxy-2-naphthoic acid (hereinafter referred to as 5BC) (TPP). / 5BC molar ratio 1.17 molar ratio), heated to 115 ° C., and reacted at this temperature for 4 hours.
The contents became a blackish brown transparent liquid, and the reaction was completed. During this time, the end reaction 5BC was analyzed by liquid chromatography to determine the end point of the reaction.
Subsequently, 630 g of methanol water (methanol concentration 90% by weight) was dropped into the contents, and 610 ml of water was further dropped. After cooling to room temperature, the precipitate was filtered off, washed with warm water and dried to obtain 126 g of the desired 5-isobutoxycarbonylamino-1-hydroxy-2-naphthoic acid phenyl ester. The yield was 93.8%. The melting point of this product was 150 to 151 ° C., and the result of composition analysis by liquid chromatography was 99.4%.
[0019]
Example 4
To 107 g of 5BC, 128 g of TPP and 500 ml of toluene as a solvent were added, and the reaction was carried out in the same manner as in Example 1. The contents were dropped into 1000 ml of water, and toluene was distilled off by steam distillation. After cooling to room temperature, the precipitate was filtered off, washed with water and dried to obtain 127 g (yield 94.9%) of the desired 5-isobutoxycarbonylamino-1-hydroxy-2-naphthoic acid phenyl ester. As a result of composition analysis by liquid chromatography, the purity was 97.3%.
[0020]
Example 5
To 5BC107g, TPP128g and phenol 89g were charged, heated up to 130 ° C, and reacted at this temperature for 4 hours. 116 g (yield: 86.3%) of the desired 5-isobutoxycarbonylamino-1-hydroxy-2-naphthoic acid phenyl ester was obtained by the same extraction method as in Example 1. As a result of composition analysis by liquid chromatography, the purity was 98.6%.
[0021]
Comparative Example 1
5BC107g, phenol 36.5g, and dimethylformamide 300g were prepared, 50.4g of thionyl chloride was dripped at the temperature of 70-80 degreeC, and reaction was performed at this temperature for 2 hours.
The contents were dropped into 1000 ml of water, the precipitate was filtered off, washed with water and dried. 94 g (yield 70.2%) of the desired 5-isobutoxycarbonylamino-1-hydroxy-2-naphthoic acid phenyl ester was obtained. As a result of composition analysis by liquid chromatography, the purity was 96.8%.
[0022]
Example 6
A reactor having a capacity of 21 with a stirrer was charged with 186 g of tri (4-methylphenyl) phosphite, 100 g of paracresol, and 135 g of 8-bromo-5-isobutoxycarbonylamino-1-hydroxy-2-naphthoic acid, up to 120 ° C. The temperature was raised by heating, and the reaction was carried out at this temperature for 4 hours. The contents became a blackish brown transparent liquid, and the reaction was completed. After confirming the end point of the reaction by liquid chromatography, 900 g of methanol water (methanol concentration 90% by weight) was added dropwise to the contents and cooled to room temperature. The precipitate was filtered off, further washed with water and dried, and 130 g (yield 77.9) of the desired 8-bromo-5-isobutoxycarbonylamino-1-hydroxy-2-naphthoic acid (4′-methylphenyl) ester was obtained. %). As a result of composition analysis by liquid chromatography, the purity was 95.2%.
[0023]
Example 7
128 g of TPP, 89 g of phenol, and 127.2 g of 5-isobutoxycarbonylamino-7-tbutyl-1-hydroxy-2-naphthoic acid were charged, heated to 115 ° C., and reacted at this temperature for 4 hours. The contents became a blackish brown transparent liquid, and the reaction was completed. After confirming the end point of the reaction by liquid chromatography, 630 g of methanol water (methanol concentration 90% by weight) was added dropwise to the contents, and 610 ml of water was further added dropwise. After cooling to room temperature, the precipitate was filtered off, washed with warm water and dried to give 143 g of the desired 5-isobutoxycarbonylamino-7-tbutyl-1-hydroxy-2-naphthoic acid phenyl ester (yield 92. 8%). As a result of composition analysis by liquid chromatography, the purity was 99.0%.
[0024]
【The invention's effect】
According to the present invention, there is an effect that an aryl naphthoate derivative useful as a synthetic intermediate for photographic drugs, dyes, and pigments can be produced industrially advantageously with high purity and high yield.
Claims (3)
で示されるナフトエ酸誘導体と、一般式（２）
で示されるトリアリール亜リン酸エステルとを、ナフトエ酸誘導体に対して、トリアリール亜リン酸エステルを１．０〜１．５モル比用いて、触媒の不存在下、反応温度 110 ℃から 130 ℃の範囲で、反応溶媒の存在又は不存在下に反応させることを特徴とする一般式（３）
で示されるナフトエ酸アリールエステル誘導体の製造方法。General formula (1)
A naphthoic acid derivative represented by the general formula (2)
In the absence of a catalyst, the reaction temperature is 110 ° C. to 130 ° C. in the absence of a catalyst using the triaryl phosphite represented by the formula (1) in a 1.0 to 1.5 molar ratio of the triaryl phosphite to the naphthoic acid derivative The reaction is carried out in the presence or absence of a reaction solvent in the range of ° C.
The manufacturing method of the naphthoic-acid arylester derivative shown by these.
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| JP03335199A JP4182271B2 (en) | 1999-01-01 | 1999-01-01 | Method for producing naphthoic acid aryl ester derivative |
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| JP03335199A JP4182271B2 (en) | 1999-01-01 | 1999-01-01 | Method for producing naphthoic acid aryl ester derivative |
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