JPS623831B2 - - Google Patents
Info
- Publication number
- JPS623831B2 JPS623831B2 JP54090315A JP9031579A JPS623831B2 JP S623831 B2 JPS623831 B2 JP S623831B2 JP 54090315 A JP54090315 A JP 54090315A JP 9031579 A JP9031579 A JP 9031579A JP S623831 B2 JPS623831 B2 JP S623831B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- methoxy
- formula
- compound
- haloterephthalic
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- OLMQISLUSGXVHK-UHFFFAOYSA-N 2-chloro-5-methoxy-4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC(Cl)=C(C(O)=O)C=C1OC OLMQISLUSGXVHK-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- GCMDWCFZPCAKNU-UHFFFAOYSA-N 2-chloro-4-ethoxycarbonyl-5-methoxybenzoic acid Chemical compound CCOC(=O)C1=CC(Cl)=C(C(O)=O)C=C1OC GCMDWCFZPCAKNU-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- PNHWBYBLVPVGEA-UHFFFAOYSA-N 2-chloro-5-methoxyterephthalic acid Chemical compound COC1=CC(C(O)=O)=C(Cl)C=C1C(O)=O PNHWBYBLVPVGEA-UHFFFAOYSA-N 0.000 description 3
- -1 2-methoxy-5-chlorosalicylic acid methyl ester Chemical compound 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001733 carboxylic acid esters Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- KPUNOVLMCQQCSK-UHFFFAOYSA-N diazomethane;ethoxyethane Chemical compound C=[N+]=[N-].CCOCC KPUNOVLMCQQCSK-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、新規なテレフタル酸誘導体およびそ
の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel terephthalic acid derivative and a method for producing the same.
本発明の新規なテレフタル酸誘導体は、一般式
（式中、Ｒは低級アルキル基、Ｘはハロゲンを表
わす。）
で示される２−メトキシ−５−ハロテレフタル酸
−１−アルキルエステルである。 The novel terephthalic acid derivatives of the present invention have the general formula (In the formula, R represents a lower alkyl group and X represents a halogen.) It is a 2-methoxy-5-haloterephthalic acid-1-alkyl ester represented by the following formula.
この化合物は、医薬品製造の中間物質として極
めて有用である。たとえば、この化合物の４位の
カルボキシル基をアミド基となし、次いで１位の
カルボン酸エステルに非対称ジアミン、たとえば
Ｎ・Ｎ−ジエチルエチレンジアミン等を作用さ
せ、最後に４位のアミド基をアミノ基に変換させ
ることにより得られる２−メトキシ−４−アミノ
−５−クロロ−Ｎ−（第３アミノエチル）−ベンツ
アミドは、鎮痛、鎮静、神経弛緩、精神緊張低下
等に薬理作用を呈する有用な医薬品である。 This compound is extremely useful as an intermediate in pharmaceutical manufacturing. For example, the carboxyl group at position 4 of this compound is converted into an amide group, then the carboxylic acid ester at position 1 is treated with an asymmetric diamine such as N/N-diethylethylenediamine, and finally the amide group at position 4 is converted into an amino group. 2-Methoxy-4-amino-5-chloro-N-(tertiary aminoethyl)-benzamide obtained by this conversion is a useful drug that exhibits pharmacological effects such as analgesia, sedation, nerve relaxation, and decreased mental tone. It is.
上記一般式において、Ｒで表わされる低級アル
キル基としては、C1〜４のアルキル基が好まし
く、具体的には、メチル基、エチル基、プロピル
基、イソプロピル基、ブチル基、イソブチル基等
が挙げられる。Ｘで表わされるハロゲンとして
は、フツ素、塩素、臭素等が挙げられ、特に塩素
が好ましい。 In the above general formula, the lower alkyl group represented by R is preferably a C1-4 alkyl group, and specific examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, etc. . Examples of the halogen represented by X include fluorine, chlorine, and bromine, with chlorine being particularly preferred.
本発明の新規なテレフタル酸誘導体のうち、特
に好ましいものは、２−メトキシ−５−クロロテ
レフタル酸−１−メチルエステルおよび２−メト
キシ−５−クロロテレフタル酸−１−エチルエス
テルである。 Among the novel terephthalic acid derivatives of the present invention, particularly preferred are 2-methoxy-5-chloroterephthalic acid-1-methyl ester and 2-methoxy-5-chloroterephthalic acid-1-ethyl ester.
本発明のもう一つの発明は、一般式
（式中、Ｘは前記と同じ意味を表わす。）
で示される２−メトキシ−５−ハロテレフタル酸
をアルコール中で反応させるか、ジアゾメタンあ
るいは低級アルキルハライドと反応させることを
特徴とする一般式
（式中、ＲおよびＸは前記と同じ意味を表わす。）
で示される新規化合物２−メトキシ−５−ハロテ
レフタル酸−１−アルキルエステルの製造法であ
る。 Another invention of the present invention is the general formula (In the formula, X represents the same meaning as above.) A general formula characterized by reacting 2-methoxy-5-haloterephthalic acid represented by the following in an alcohol or with diazomethane or a lower alkyl halide. (In the formula, R and X have the same meanings as above.) This is a method for producing a novel compound 2-methoxy-5-haloterephthalic acid-1-alkyl ester represented by the following formula.
この製造法の具体的な一例を説明すると、次の
とおりである。 A specific example of this manufacturing method is as follows.
すなわち、原料物質２−メトキシ−５−ハロテ
レフタル酸を低級アルコール、たとえば、メタノ
ール、エタノール、プロパノール、イソプロパノ
ール等を溶媒とし、適当な酸触媒、たとえば硫
酸、塩酸等の鉱酸あるいはｐ−トルエンスルホン
酸、BF3、AlCl3などのルイス酸の存在下反応さ
せるか、他の有機溶媒、たとえば、アセトン、ベ
ンゼン、トルエン等を溶媒として、エステル化
剤、たとえば、ジアゾメタン、ハロゲン化アルキ
ル等を反応させることにより得られる。この反応
における温度は、−20℃ないし150℃であり、好ま
しくは15℃ないし60℃、反応時間は１時間ないし
20時間、好ましくは４〜６時間程度である。 That is, the raw material 2-methoxy-5-haloterephthalic acid is used as a solvent in a lower alcohol such as methanol, ethanol, propanol, isopropanol, etc., and in a suitable acid catalyst such as a mineral acid such as sulfuric acid or hydrochloric acid or p-toluenesulfonic acid. , BF 3 , AlCl 3 or other Lewis acid, or react with an esterifying agent such as diazomethane, alkyl halide, etc. in another organic solvent such as acetone, benzene, toluene, etc. It is obtained by The temperature in this reaction is -20°C to 150°C, preferably 15°C to 60°C, and the reaction time is 1 hour to 150°C.
It is about 20 hours, preferably about 4 to 6 hours.
以下、実施例を挙げて説明するが、本発明は、
これらに限定されるものではない。 The present invention will be described below with reference to Examples.
It is not limited to these.
実施例 １
２−メトキシ−５−クロロテレフタル酸−１−
メチルエステルの製造法：
２−メトキシ−５−クロロテレフタル酸11.5ｇ
を無水メタノール200c.c.に溶解する。この溶解液
に濃硫酸7.7c.c.を冷却しながら１時間かけて滴下
する。滴下後、温度を30℃付近に保つて５時間撹
拌を行う。得られた反応液を800ｇの氷水中に投
入し、1000c.c.のエーテルで抽出、エーテル層を５
％アンモニア水500c.c.で抽出する。得られた水層
を５％塩酸で酸性化すると、新規化合物２−メト
キシ−５−クロロテレフタル酸−１−メチルエス
テルの結晶が析出するので、これを取する。Example 1 2-methoxy-5-chloroterephthalic acid-1-
Manufacturing method of methyl ester: 11.5 g of 2-methoxy-5-chloroterephthalic acid
Dissolve in 200 c.c. of absolute methanol. 7.7 cc of concentrated sulfuric acid is added dropwise to this solution over 1 hour while cooling. After dropping, the mixture was stirred for 5 hours while keeping the temperature around 30°C. The resulting reaction solution was poured into 800 g of ice water, extracted with 1000 c.c. of ether, and the ether layer was
Extract with 500c.c.% ammonia water. When the obtained aqueous layer is acidified with 5% hydrochloric acid, crystals of the new compound 2-methoxy-5-chloroterephthalic acid-1-methyl ester are precipitated, and these are collected.
収量11.2ｇ（収率92％） 本品は融点152〜153℃を示す白色結晶である。 Yield 11.2g (yield 92%) This product is a white crystal with a melting point of 152-153℃.
IRスペクトル
3000cm-1〜2000cm-1 −COOH
1730cm-1 −COOCH3
1700cm-1 −COOH由来の＞Ｃ＝０
元素分析値 C10H9ClO5として
理論値 Ｃ；49.10 Ｈ；3.68 Cl；14.49
実測値 Ｃ；48.97 Ｈ；3.68 Cl；14.36
実施例 ２
２−メトキシ−５−クロロサリチル酸メチルエ
ステルの製造：
実施例１で得た２−メトキシ−５−クロロテレ
フタル酸−１−メチルエステル0.12ｇを水200c.c.
に溶解後、酢酸バリウム0.25ｇを含む水溶液50c.c.
を加え、20〜25℃にて１時間撹拌する。得られた
反応液を減圧下蒸発させると、白色粉末0.35ｇを
得る。この白色粉末を170℃に加熱した電気炉に
て１時間加熱すると、加熱の初期において激しく
発泡を伴い脱炭酸反応が起り、黒かつ色粉末とな
る。この粉末を水にデスラリーした後、１規定塩
酸で中和し、酢酸エチル100c.c.で抽出する。得ら
れた酢酸エチル層から２−メトキシ−５−クロロ
サルチル酸メチルエステルが黄色オイル状物（沸
点235〜240℃）として得られた。IR spectrum 3000cm -1 ~2000cm -1 -COOH 1730cm -1 -COOCH 3 1700cm -1 >C=0 derived from -COOH Elemental analysis value C 10 H 9 ClO 5 Theoretical value C; 49.10 H; 3.68 Cl; 14.49 Actual measurement Value C; 48.97 H; 3.68 Cl; 14.36 Example 2 Production of 2-methoxy-5-chlorosalicylic acid methyl ester: 0.12 g of 2-methoxy-5-chloroterephthalic acid-1-methyl ester obtained in Example 1 was added to water. 200c.c.
After dissolving in 50 c.c. of an aqueous solution containing 0.25 g of barium acetate.
and stir at 20-25°C for 1 hour. The resulting reaction solution is evaporated under reduced pressure to obtain 0.35 g of white powder. When this white powder is heated for 1 hour in an electric furnace heated to 170°C, a decarboxylation reaction occurs accompanied by intense foaming at the initial stage of heating, resulting in a black colored powder. This powder was deslurried in water, neutralized with 1N hydrochloric acid, and extracted with 100 c.c. of ethyl acetate. From the obtained ethyl acetate layer, 2-methoxy-5-chlorosalicylic acid methyl ester was obtained as a yellow oil (boiling point 235-240°C).
元素分析値 C9H9ClO3として
理論値 Ｃ；53.88 Ｈ；4.52 Cl；17.67
実測値 Ｃ；52.80 Ｈ；4.50 Cl；17.14
本実施例で得られた２−メトキシ−５−クロロ
サルチル酸メチルエステルは、上述元素分析をは
じめ、IR、NMR分析で標品と完全に一致した。
したがつて、本実施例より実施例１で得られた化
合物は、２−メトキシ−５−クロロテレフタル酸
−１−メチルエステルであることが完全に裏づけ
られた。Elemental analysis value C 9 H 9 ClO 3 Theoretical value C; 53.88 H; 4.52 Cl; 17.67 Actual value C; 52.80 H; 4.50 Cl; 17.14 2-methoxy-5-chlorosalicylic acid methyl ester obtained in this example In addition to the above-mentioned elemental analysis, IR and NMR analysis completely matched the sample.
Therefore, this example completely confirmed that the compound obtained in Example 1 was 2-methoxy-5-chloroterephthalic acid-1-methyl ester.
実施例 ３
２−メトキシ−５−クロロテレフタル酸−１−
メチルエステルの製造：
２−メトキシ−５−クロロテレフタル酸23ｇを
無水メタノール500c.c.中に溶解させる。この溶液
にジアゾメタン4.2ｇを含むジアゾメタンエーテ
ル溶液500c.c.を室温下加える。１時間放置後溶媒
を減圧下留去し、2000c.c.のエーテルに溶解する。
以下実施例１と同様の操作を行なうと、新規化合
物２−メトキシ−５−クロロテレフタル酸−１−
メチルエステル20.7ｇを得る。Example 3 2-methoxy-5-chloroterephthalic acid-1-
Preparation of methyl ester: 23 g of 2-methoxy-5-chloroterephthalic acid are dissolved in 500 c.c. of anhydrous methanol. To this solution was added 500 c.c. of a diazomethane ether solution containing 4.2 g of diazomethane at room temperature. After standing for 1 hour, the solvent was distilled off under reduced pressure, and the solution was dissolved in 2000 c.c. of ether.
Following the same procedure as in Example 1, a new compound 2-methoxy-5-chloroterephthalic acid-1-
20.7 g of methyl ester are obtained.
実施例 ４
２−メトキシ−５−ハロテレフタル酸−１−エ
チルエステルの製造：
２−メトキシ−５−クロロテレフタル酸4.6ｇ
をアセトン100c.c.に溶解し、これに炭酸カリウム
1.8ｇを加える。次いでヨウ化エチル6.2ｇを含む
アセトン溶液50c.c.を加え、３時間加熱還流する。
反応後減圧下で溶媒を留去し、残留物を水200c.c.
に溶解する。以下実施例１と同様の操作を行なう
と、新規化合物２−メトキシ−５−クロロテレフ
タル酸−１−メチルエステル4.7ｇを得る。Example 4 Production of 2-methoxy-5-haloterephthalic acid-1-ethyl ester: 4.6 g of 2-methoxy-5-chloroterephthalic acid
Dissolve in 100c.c. of acetone and add potassium carbonate to this.
Add 1.8g. Next, 50 c.c. of an acetone solution containing 6.2 g of ethyl iodide was added, and the mixture was heated under reflux for 3 hours.
After the reaction, the solvent was distilled off under reduced pressure, and the residue was mixed with 200 c.c. of water.
dissolve in The same operations as in Example 1 were carried out to obtain 4.7 g of the new compound 2-methoxy-5-chloroterephthalic acid-1-methyl ester.
元素分析値 C11H11ClO5として 理論値 Ｃ；51.08 Ｈ；4.29 Cl；13.71 実測値 Ｃ；50.06 Ｈ；4.20 Cl；13.25Elemental analysis value C 11 H 11 ClO As 5 Theoretical value C; 51.08 H; 4.29 Cl; 13.71 Actual value C; 50.06 H; 4.20 Cl; 13.25
Claims (1)
わす。） で示される新規化合物２−メトキシ−５−ハロテ
レフタル酸−１−アルキルエステル。 ２ ＲがC1〜４のアルキル基である特許請求の
範囲第１項記載の化合物。 ３ Ｘが塩素である特許請求の範囲第１項記載の
化合物。 ４ 新規化合物が２−メトキシ−５−クロロテレ
フタル酸−１−メチルエステルである特許請求の
範囲第１項記載の化合物。 ５ 新規化合物が２−メトキシ−５−クロロテレ
フタル酸−１−エチルエステルである特許請求の
範囲第１項記載の化合物。 ６ 一般式 （式中、Ｘはハロゲンを表わす。） で示される２−メトキシ−５−ハロテレフタル酸
をアルコール中で反応させるか、ジアゾメタンあ
るいは低級アルキルハライドと反応させることを
特徴とする一般式 （式中、Ｒは低級アルキル基、Ｘは前記と同じ意
味を表わす。） で示される新規化合物２−メトキシ−５−ハロテ
レフタル酸−１−アルキルエステルの製造法。[Claims] 1. General formula (In the formula, R represents a lower alkyl group and X represents a halogen.) A novel compound 2-methoxy-5-haloterephthalic acid-1-alkyl ester. 2. The compound according to claim 1, wherein R is a C1-4 alkyl group. 3. The compound according to claim 1, wherein X is chlorine. 4. The compound according to claim 1, wherein the new compound is 2-methoxy-5-chloroterephthalic acid-1-methyl ester. 5. The compound according to claim 1, wherein the new compound is 2-methoxy-5-chloroterephthalic acid-1-ethyl ester. 6 General formula (In the formula, X represents a halogen.) A general formula characterized by reacting 2-methoxy-5-haloterephthalic acid represented by the following in an alcohol or with diazomethane or a lower alkyl halide. (In the formula, R is a lower alkyl group, and X has the same meaning as above.) A method for producing a novel compound 2-methoxy-5-haloterephthalic acid-1-alkyl ester represented by the following formula.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9031579A JPS5616446A (en) | 1979-07-18 | 1979-07-18 | Novel derivative of terephthalic acid and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9031579A JPS5616446A (en) | 1979-07-18 | 1979-07-18 | Novel derivative of terephthalic acid and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5616446A JPS5616446A (en) | 1981-02-17 |
| JPS623831B2 true JPS623831B2 (en) | 1987-01-27 |
Family
ID=13995088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9031579A Granted JPS5616446A (en) | 1979-07-18 | 1979-07-18 | Novel derivative of terephthalic acid and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5616446A (en) |
-
1979
- 1979-07-18 JP JP9031579A patent/JPS5616446A/en active Granted
Non-Patent Citations (1)
| Title |
|---|
| CHEM PHARM BULL * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5616446A (en) | 1981-02-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0148911B2 (en) | ||
| JPS6121637B2 (en) | ||
| JPS623831B2 (en) | ||
| US3238201A (en) | Isatoic anhydride derivatives | |
| JP4173599B2 (en) | Process for producing 6-hydroxy-2-oxo-1,2,3,4-tetrahydroquinoline | |
| JPH0352881A (en) | Preparation of tetronic alkylate | |
| JPH0522709B2 (en) | ||
| US4213905A (en) | Preparation of 5-aroyl-1-loweralkylpyrrole-2-acetic acid salts | |
| EP0047674A1 (en) | Novel process for preparing isoindolin derivatives | |
| CA1054630A (en) | Substituted indanylpropionic acids | |
| JPS6154016B2 (en) | ||
| JPS6327337B2 (en) | ||
| KR100699457B1 (en) | Process for preparing dibenzothiepin derivatives and intermediates thereof | |
| JP3563424B2 (en) | Method for producing 4H-pyran-4-one | |
| EP0000152A1 (en) | Oxaminic acids and esters, process for their preparation and pharmaceutical compositions containing them | |
| KR900001078B1 (en) | A preparation process for cyclo quinolone derivatives | |
| JP3876933B2 (en) | Method for producing hydrogen sulfate ester | |
| CA1060904A (en) | Preparation of indanylpropionic acids | |
| JPS623830B2 (en) | ||
| KR100529157B1 (en) | A preparing process for aromatic propionic acid | |
| SU327678A1 (en) | METHOD FOR PRODUCING DERIVATIVES OF AZEPIN | |
| EP0396014A2 (en) | Substituted biphenylcarboxylic acids, process for their preparation and new intermediates | |
| US4208526A (en) | Process for the preparation of thiazolidin-4-one-acetic acid derivatives | |
| KR910009236B1 (en) | Process for the preparation of n-2'-carboxyl phenyl-4-chloro anthranilic acid | |
| JPH0583537B2 (en) |