JPH01175968A - Production of pyridinecarboxylic acid esters - Google Patents
Production of pyridinecarboxylic acid estersInfo
- Publication number
- JPH01175968A JPH01175968A JP33372587A JP33372587A JPH01175968A JP H01175968 A JPH01175968 A JP H01175968A JP 33372587 A JP33372587 A JP 33372587A JP 33372587 A JP33372587 A JP 33372587A JP H01175968 A JPH01175968 A JP H01175968A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- pyridine
- compound shown
- acid
- general formula
- 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
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title description 7
- 239000000126 substance Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- SQCOEUUTSVPTAE-UHFFFAOYSA-N 2h-pyridine-1-carboxamide Chemical class NC(=O)N1CC=CC=C1 SQCOEUUTSVPTAE-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 10
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 abstract description 9
- 239000006227 byproduct Substances 0.000 abstract description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 6
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 abstract description 5
- 230000002378 acidificating effect Effects 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 4
- 229910021529 ammonia Inorganic materials 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 2
- 239000011707 mineral Substances 0.000 abstract description 2
- 150000007524 organic acids Chemical class 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- -1 lysine carboxylic acid ester Chemical class 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 235000001968 nicotinic acid Nutrition 0.000 description 4
- 239000011664 nicotinic acid Substances 0.000 description 4
- 229960003512 nicotinic acid Drugs 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HZUPDAXALKWCGX-UHFFFAOYSA-N Butyl pyridine-2-carboxylate Chemical compound CCCCOC(=O)C1=CC=CC=N1 HZUPDAXALKWCGX-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- NMMIHXMBOZYNET-UHFFFAOYSA-N Methyl picolinate Chemical compound COC(=O)C1=CC=CC=N1 NMMIHXMBOZYNET-UHFFFAOYSA-N 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 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
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
- 229960001238 methylnicotinate Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分厨］
本発明は、ピリジンカルボン酸エステル類の新規な製法
に関するものであり、更に詳しくは、−最大（１）：
（式中、Ｒは炭素数１〜４のアルキル基を表わす）で示
されるビリジンカルホキシミダート類を出発物質とする
一般式（２）：
（式中、Ｒは前記に同じ）で示されるピリジンカルボン
酸エステル類の製法に関するものである。Detailed Description of the Invention [Industrial Utilization] The present invention relates to a new method for producing pyridine carboxylic acid esters, and more specifically, -maximum (1): (wherein R is carbon A method for producing pyridine carboxylic acid esters represented by the general formula (2) using as a starting material pyridine carboximidates (representing an alkyl group of numbers 1 to 4): (wherein R is the same as above) It is related to.
−・最大（２）で示されるピリジンカルボン酸エステル
類は、医桑合成用中間体、農薬合成用中間体など各種薬
品合成中間体として多用な用途が期待される右用な化合
物である。Pyridine carboxylic acid esters represented by - maximum (2) are useful compounds that are expected to have a wide range of uses as intermediates for the synthesis of various drugs, such as intermediates for the synthesis of medical mulberry plants and intermediates for the synthesis of agricultural chemicals.
［従来技術］
従来、−最大（２）で、示されるとリジンカルボン酸エ
ステルの製法としては、■塩化チオニル（又はオキシ塩
化リン）を用いて、ニコチン酸より合成したニコチン酸
クロライドをアルコールでエステル化する方法 （ジャ
ーナル オブ アメリカン ケミカル ソ号イエティ５
−６２４２５−２４２７［１９３４］ ） 、また０１
８０℃という高温にてニコチン酸をアルコールでエステ
ル化する方法（ドイツ特許第９４２．５０９号）が知ら
れている。[Prior art] Conventionally, the method for producing lysine carboxylic acid ester at maximum (2) is: ■ Using thionyl chloride (or phosphorus oxychloride), nicotinic acid chloride synthesized from nicotinic acid is esterified with alcohol. (Journal of American Chemical
-62425-2427 [1934] ), also 01
A method is known in which nicotinic acid is esterified with alcohol at a high temperature of 80° C. (German Patent No. 942.509).
［発明が解決しようとする問題点］
しかしながら、前記■の方法は、出発物質であるニコチ
ン酸クロライドを５２造するのに、３−シアノピリジン
から出発した場合、３−シアノピリジンをニコチン酸に
転化する工程、次いでニコチン酸をニコチン酸クロライ
ドに転化する工程からなる２工程を必要とするので、工
業的に実施するには有利な方法とは言い難い、また、前
記■の方法は反応に高温を要するので、省資源の点から
工業製法として満足できるものではない。[Problems to be Solved by the Invention] However, in the method (2) above, when starting from 3-cyanopyridine to produce nicotinic acid chloride as a starting material, 3-cyanopyridine is converted to nicotinic acid. Since it requires two steps: a step of converting nicotinic acid into nicotinic acid chloride, it cannot be said that it is an advantageous method for industrial implementation. Therefore, it is not satisfactory as an industrial manufacturing method from the point of view of resource saving.
本発明の目的はかかる問題点を解決しつる一般式（２）
で示されるピリジンカルボン酸エステルの新規な製造法
を提供することにある。The purpose of the present invention is to solve such problems by formula (2)
An object of the present invention is to provide a new method for producing a pyridine carboxylic acid ester represented by:
［問題点を解決するための手段］
本発明者らは工業的に有利な一般式（２）で示されるピ
リジンカルボン酸エステル類の製法を確立すべく鋭意研
究を重ねた結果、容易に製造されつるピリジンカルホキ
シミダート類を出発物質とし、これが常温下であっても
容易に加水分解され好収率でピリジンカルボン酸エステ
ル類を与えることを見出し本発明を完成した。[Means for Solving the Problems] The present inventors have conducted extensive research to establish an industrially advantageous method for producing pyridine carboxylic acid esters represented by general formula (2), and have found that they can be easily produced. Using vine pyridine carboximidates as a starting material, they found that they can be easily hydrolyzed to give pyridine carboxylic acid esters in good yield even at room temperature, and have completed the present invention.
即ち本発明は、
一般式（１）：
（式中、Ｒは炭素数１〜４のアルキル基を表わす）で示
されるビリジンカルホキシミダート類を加水分解するこ
とを特徴とする
一般式（２）：
（式中、Ｒは前記に同じ）で示されるピリジンカルボン
酸エステル類の製法に関するものである。That is, the present invention provides a compound of the general formula (2), which is characterized by hydrolyzing a pyridine carboximidate represented by the general formula (1): (wherein, R represents an alkyl group having 1 to 4 carbon atoms). ): (in the formula, R is the same as above).
本発明で使用する一般式（１）で示されるビリジンカル
ホキシミダート類は触媒量のアルカリ金属アルコラード
の存在下、常温で一般式（３）：で示されるシアノピリ
ジン類と一般式（４）：ＲＯＨ（４）
（式中、Ｒは前記に同じ）で示されるアルコールを反応
させることによりｌ工程で容易に得られる。The pyridine carboximidates represented by the general formula (1) used in the present invention are combined with the cyanopyridines represented by the general formula (3) and the general formula (4) at room temperature in the presence of a catalytic amount of alkali metal alcoholade. :ROH (4) (In the formula, R is the same as above) can be easily obtained in step 1 by reacting the alcohol.
一般式（Ｉン、（２）及び（４）におけるＲは炭素数１
〜４のアルキル基であり、具体的には、メチル基、エチ
ル基、プロピル基、ブチル基の直鎖状アルキル基、イソ
プロピル基、イソブチル基などの分岐を有するアルキル
基が挙げられる。R in the general formula (In, (2) and (4) has 1 carbon number
-4 alkyl groups, and specifically include linear alkyl groups such as methyl, ethyl, propyl, and butyl groups, and branched alkyl groups such as isopropyl and isobutyl groups.
本発明の方法を実施するには、通常、酸を使用して一般
式（１）で示されるビリジンカルホキシミダート類を加
水分解すれば良い。To carry out the method of the present invention, it is usually sufficient to hydrolyze the pyridine carboximidate represented by the general formula (1) using an acid.
本発明の方法は、常温付近で１〜３時間程度の短時間加
水分解を行なえば充分である。このように反応温度は、
常温付近で充分であるが、それ以−Ｆ及びそれ以下の温
度であっても差し支えない。In the method of the present invention, it is sufficient to carry out hydrolysis for a short time of about 1 to 3 hours at around room temperature. In this way, the reaction temperature is
A temperature around room temperature is sufficient, but temperatures above -F and lower are also acceptable.
本発明の加水分解に使用する水の量は、化学ｍ論Ｍ以上
であれば特に限定されるものではない。The amount of water used in the hydrolysis of the present invention is not particularly limited as long as it is at least M in chemical theory.
本発明に使用される酸性物質としては、本発明方法にお
いて副生ずるアンモニアを捕捉できるものであれば特に
限定されないが、例えば塩酸、硫酸、燐酸、などの鉱酸
、ｐ−トルエンスルホン酸、蟻酸などの有機酸などが使
用される。酸性物質の使用量は副生ずるアンモニアを捕
捉できる量販上であれば良い。The acidic substance used in the present invention is not particularly limited as long as it can capture ammonia produced as a by-product in the method of the present invention, but examples include mineral acids such as hydrochloric acid, sulfuric acid, and phosphoric acid, p-toluenesulfonic acid, and formic acid. organic acids, etc. are used. The amount of acidic substance used may be as long as it can capture the by-product ammonia.
本発明に有機溶媒を併用しても差し支えない。An organic solvent may be used in combination with the present invention.
かかる溶媒としては本発明の加水分解に不活性なもので
あれば良く、例えばアルコール、ベンセン、トルエン、
などが挙げられる。有機溶媒の使用量は特に限定される
ものではないが、通常は、−最大（１）で示されるビリ
ジン力ルポキシミダ−ト類の使用量の１倍から５倍重量
部程度である。一般式（１）で示されるビリジンカルホ
キシミダート類として、一般式（３）で表わされるシア
ノピリジン類と一般式（４）で示されるアルコール類を
反応させて、当該ビリジンカルホキシミダート類を単離
することなく、得られる反応液をそのまま用いることが
できる。Such a solvent may be any solvent as long as it is inert to the hydrolysis of the present invention, such as alcohol, benzene, toluene,
Examples include. The amount of the organic solvent to be used is not particularly limited, but it is usually about 1 to 5 parts by weight of the amount of the pyridine lupoximidate used as shown in -maximum (1). The pyridine carboximidates represented by the general formula (1) are prepared by reacting the cyanopyridines represented by the general formula (3) with the alcohols represented by the general formula (4). The resulting reaction solution can be used as it is without isolating.
本発明の好ましい一実施態様を挙げれば、一般式（＋）
で示されるビリジンカルホキシミダート類の水溶液又は
アルコール溶液に、当量の酸性物質の水溶液を加え、常
温で１〜３時間攪拌すれば良い。In a preferred embodiment of the present invention, the general formula (+)
An equivalent amount of an aqueous solution of an acidic substance may be added to an aqueous or alcoholic solution of a pyridine carboximidate represented by the formula, and the mixture may be stirred at room temperature for 1 to 3 hours.
本発明の一般式（２）で示されるピリジンカルボン酸エ
ステル類は、加水分解終了後副生ずる無機塩をろ別し、
ろ液を濃縮蒸留することにより、加水分解終了液から容
易に単離ｙ１製される。The pyridine carboxylic acid esters represented by the general formula (2) of the present invention are obtained by filtering off the inorganic salts produced as a by-product after the completion of hydrolysis.
By concentrating and distilling the filtrate, the product y1 can be easily isolated from the hydrolyzed solution.
［実施例］
次に実施例を挙げて本発明を更に詳しく説明するが本発
明はこれらに限定されるものではない。[Examples] Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.
実施例１
メチル＝２−ビリジン力ルポキシミダート１３６ｇとメ
タノール４８０ｇから成る溶液に３６％塩酸水溶液１０
１．４ｇを加え、常温で１時間３０分攪拌した後副生ず
る無機塩をろ別した。ろ液を濃縮、蒸留してピコリン酸
メチル１２４ｇ（ｂ、ｐ１□１１７℃、メチル＝２−ビ
リジン力ルポキシミダートからの収率９０．７％）を得
た。Example 1 To a solution consisting of 136 g of methyl 2-pyridine lupoximidate and 480 g of methanol was added 10 g of a 36% aqueous hydrochloric acid solution.
After adding 1.4 g and stirring at room temperature for 1 hour and 30 minutes, by-product inorganic salts were filtered off. The filtrate was concentrated and distilled to obtain 124 g of methyl picolinate (b, p1 117°C, yield 90.7% from methyl 2-pyridine rupoximidate).
実施例２
メチル＝３−ピリジン力ルポキシミダート１３６ｇとメ
タノール４８０ｇから成る溶液に３３％硫酸水溶液１４
８．５ｇを加え、常温で１時間攪拌した後副生ずる無機
塩をろ別した。ろ液を濃縮、蒸留して、ニコチン酸メチ
ル１２０゜４ｇ（ｂ、ｐ、＊。１０７．５℃、メチル＝
３−ピリジン力ルポキシミダートからの収率８７．９％
）を得た。Example 2 To a solution consisting of 136 g of methyl 3-pyridine lupoximidate and 480 g of methanol was added 14% of a 33% aqueous sulfuric acid solution.
After 8.5 g of the mixture was added and stirred at room temperature for 1 hour, by-product inorganic salts were filtered off. The filtrate was concentrated and distilled to give 120°4 g of methyl nicotinate (b, p, *. 107.5°C, methyl =
Yield from 3-pyridine lupoximidate 87.9%
) was obtained.
実施例３
メチル＝４−ビリジン力ルポキシミダート１３６ｇとメ
タノール４８０ｇから成る溶液に３３％硫酸水溶液１４
８．５ｇを加え、常温で１時間攪拌した後副生ずる無機
塩をろ別した。ろ液を濃縮、蒸留してイソニコチン酸メ
チル１１５−８ ｇ （ｂ、Ｉ）、＋ａ、ｓｌ Ｏ２℃
、メチル＝４−ビリジン力ルポキシミダートからの収率
８４．５％）を得た。Example 3 To a solution consisting of 136 g of methyl 4-pyridine lupoximidate and 480 g of methanol was added 14% of a 33% aqueous sulfuric acid solution.
After 8.5 g of the mixture was added and stirred at room temperature for 1 hour, by-product inorganic salts were filtered off. The filtrate was concentrated and distilled to give 115-8 g of methyl isonicotinate (b, I), +a, sl O2°C.
, a yield of 84.5% from methyl 4-pyridine lupoximidate was obtained.
実施例４
ブチル＝２−ビリジン力ルポキシミダート１７８ｇとブ
タノール４８０ｇから成る溶液に３３％硫酸水溶液１４
８．５ｇを加え、時間攪拌した後副生ずる無機塩をろ別
した。ろ液より分液した油層を濃縮、蒸留してピコリン
酸ブチル１７０ｇ （ｂ、ｐ、ａ １３３℃、ブチル＝
２−ビリジン力ルポキシミダートからの収率９４．９％
）を得た。Example 4 A solution of 178 g of butyl 2-pyridine lupoximidate and 480 g of butanol was added with 14% sulfuric acid aqueous solution.
After adding 8.5 g and stirring for a period of time, by-product inorganic salts were filtered off. The oil layer separated from the filtrate was concentrated and distilled to yield 170 g of butyl picolinate (b, p, a 133°C, butyl =
Yield from 2-pyridine lupoximidate 94.9%
) was obtained.
［発明の効果］
本発明の方法は、シアノピリジンから一工程で容易に得
られるピリジンカルホキシミダート類を出発原料とし、
短時間で、従来方法にくらべて極めて低い温度で、しか
も高収率でピリジンカルボン酸エステル類を製造するこ
とができる、工業的に極めて右利な方法である。[Effects of the Invention] The method of the present invention uses pyridine carboximidates, which can be easily obtained in one step from cyanopyridine, as a starting material,
This method is industrially extremely advantageous because it can produce pyridine carboxylic acid esters in a short time, at extremely low temperatures, and in high yields compared to conventional methods.
Claims (1)
されるピリジンカルボキシミダート類を加水分解するこ
とを特徴とする 一般式（２）： ▲数式、化学式、表等があります▼（２） （式中、Ｒは前記に同じ）で示されるピリジンカルボン
酸エステル類の製法[Claims] General formula (1): ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (1) Pyridine carboximidates represented by (in the formula, R represents an alkyl group having 1 to 4 carbon atoms) General formula (2) characterized by the hydrolysis of
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62333725A JP2597124B2 (en) | 1987-12-28 | 1987-12-28 | Preparation of pyridinecarboxylic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62333725A JP2597124B2 (en) | 1987-12-28 | 1987-12-28 | Preparation of pyridinecarboxylic acid esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01175968A true JPH01175968A (en) | 1989-07-12 |
| JP2597124B2 JP2597124B2 (en) | 1997-04-02 |
Family
ID=18269260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62333725A Expired - Fee Related JP2597124B2 (en) | 1987-12-28 | 1987-12-28 | Preparation of pyridinecarboxylic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2597124B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0569587A1 (en) * | 1991-01-30 | 1993-11-18 | Central Glass Company, Limited | Phthalimide compound and production thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4275069A (en) * | 1979-01-22 | 1981-06-23 | The Upjohn Company | Anti-diabetic 1,2-dihydro-2-oxo-6-alkyl-nicotinic acids |
-
1987
- 1987-12-28 JP JP62333725A patent/JP2597124B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4275069A (en) * | 1979-01-22 | 1981-06-23 | The Upjohn Company | Anti-diabetic 1,2-dihydro-2-oxo-6-alkyl-nicotinic acids |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0569587A1 (en) * | 1991-01-30 | 1993-11-18 | Central Glass Company, Limited | Phthalimide compound and production thereof |
| EP0569587A4 (en) * | 1991-01-30 | 1994-01-05 | Central Glass Company, Limited |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2597124B2 (en) | 1997-04-02 |
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