JPS62238265A - Phenylpyridine derivative - Google Patents

Phenylpyridine derivative

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Publication number
JPS62238265A
JPS62238265A JP61080726A JP8072686A JPS62238265A JP S62238265 A JPS62238265 A JP S62238265A JP 61080726 A JP61080726 A JP 61080726A JP 8072686 A JP8072686 A JP 8072686A JP S62238265 A JPS62238265 A JP S62238265A
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JP
Japan
Prior art keywords
compound
liquid crystal
formula
reacting
chiral smectic
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
Application number
JP61080726A
Other languages
Japanese (ja)
Other versions
JPH0692370B2 (en
Inventor
Kazumasa Oba
大場 和正
Yasushi Nonoguchi
野々口 泰
Masaaki Taguchi
田口 雅明
Takamasa Harada
隆正 原田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Seiko Instruments Inc
Teikoku Chemical Industry Co Ltd
Original Assignee
Seiko Instruments Inc
Teikoku Chemical Industry Co Ltd
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Application filed by Seiko Instruments Inc, Teikoku Chemical Industry Co Ltd filed Critical Seiko Instruments Inc
Priority to JP61080726A priority Critical patent/JPH0692370B2/en
Publication of JPS62238265A publication Critical patent/JPS62238265A/en
Publication of JPH0692370B2 publication Critical patent/JPH0692370B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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  • Pyridine Compounds (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

NEW MATERIAL:A phenylpyridine derivative of formula I (R* is optically active alkyl containing asymmetric carbon atom in molecular chain; R is straight-chain alkyl; R* and R may be exchanged each other). EXAMPLE:(S)-5-[4'-(2-methylbutyloxy)phenyl]-2-n-undecyloxypyridine. USE:It can be used as a liquid crystal compound or liquid crystal material and is useful for the production of a liquid crystal display element. It can be blended with a ferroelectric chiral smectic liquid crystal to give a wholly uniformized domain. Also effective in expanding the temperature range to exhibit chiral smectic C phase. PREPARATION:The compound of formula I can be produced by reacting the compound of formula II with a halogenating agent in the presence of a basic compound, reacting the product with an alkyloxy alkali metal salt and reacting the resultant compound of formula III e.g. with (S)-2-methylbutyl chloride.

Description

【発明の詳細な説明】 (産業−にの利用分野) 本発明は、液晶化合物ないしは液晶材料として使用でき
る新規な化合物の提供に係るものであって、それ自体で
又は他の液晶化合物とのブレンド1こより性能の改善を
はかるなどして液晶表示素子の作成に利用できる。
Detailed Description of the Invention (Industrial Field of Application) The present invention relates to the provision of a new compound that can be used as a liquid crystal compound or liquid crystal material, either by itself or in a blend with other liquid crystal compounds. This method can be used to improve the performance of liquid crystal display devices.

(軸間の技術) 液晶による表示素子において使用されている液晶化合物
は、ネマチック相をとる液晶が大半である。しかし、電
気光学的応答速度の点において発光型表示素子にくらべ
ると遥かに及ばず改善が試みられている。近年、応答速
度が速いことで注目されている液晶化合物に1強誘電性
液晶化合物がある0強誘電性液晶化合物としてはじめて
開発されたのは、ドデシルベンジリデン−p−アミノ−
2−メチルブチルシンナメートであって、1975年に
合成された。
(Interaxial technology) Most liquid crystal compounds used in liquid crystal display elements are liquid crystals that take a nematic phase. However, in terms of electro-optical response speed, it is far inferior to that of light-emitting display elements, and attempts are being made to improve it. In recent years, ferroelectric liquid crystal compounds have attracted attention due to their fast response speed.The first ferroelectric liquid crystal compound developed was dodecylbenzylidene-p-amino-
2-Methylbutylcinnamate, synthesized in 1975.

この化合物は、カイラルスメクチックC相をとるけれど
も、その転移温度が高いこと、従って。
Although this compound adopts a chiral smectic C phase, its transition temperature is therefore high.

室温を含む低い温度での使用は不可能であり、そのほか
に、シップ塩基を含む化合物であるため化学的安定性に
欠けるという問題を持っている。その後、数多くの強誘
電性液晶化合物が合成され、その性質の究明が行われて
いるけれども、室温を含む幅広い温度範囲で、カイラル
スメクチックC相をとる液晶化合物は知られていない。
It is impossible to use it at low temperatures, including room temperature, and it also has the problem of lacking chemical stability because it is a compound containing a ship base. Since then, many ferroelectric liquid crystal compounds have been synthesized and their properties have been investigated, but no liquid crystal compound is known that takes a chiral smectic C phase over a wide temperature range including room temperature.

液晶相の移転温度の低下又は、温度範囲の拡大のためネ
マチック液晶の分野で採用されている−般的な方法に、
いくつかの液晶化合物を混合する方法がある。
A common method employed in the field of nematic liquid crystals to lower the transition temperature or expand the temperature range of the liquid crystal phase is:
There are methods of mixing several liquid crystal compounds.

強誘電性液晶の分野においても同様の方法が検討されて
いて、試行錯誤の域を出ていない。どのような骨格を選
べば、他の液晶との相溶性が高まるか、どのような置換
基を導入すれば如何なる液晶相をとって、他の液晶の相
転移温度にどのような影響を及ぼすかといったことは、
化合物一つ一つについてデス1−シてみなければ全く判
らないといっても過言ではない。
Similar methods are being considered in the field of ferroelectric liquid crystals, and are still a matter of trial and error. What kind of skeleton should be selected to increase compatibility with other liquid crystals, what kind of substituents should be introduced to form a liquid crystal phase, and what effect will it have on the phase transition temperature of other liquid crystals? That means,
It is no exaggeration to say that you will not understand anything unless you examine each compound one by one.

本発明に係る液晶化合物と同様の骨格を持つ液晶化合物
に関する研究がなされたことが、Adv。
Adv that research has been conducted on liquid crystal compounds having the same skeleton as the liquid crystal compound according to the present invention.

Liq、  Cryst、  Rss、  Appl、
Liq, Cryst, Rss, Appl,
.

Proc、  Liq、  Cryst、  Conf
Proc, Liq, Crystal, Conf
.

Soc、  Countries、3rd  1979
゜2.1007−1.3に明らかにされている。これに
よると、得られた化合物は全て直鎖状のアルキル1&を
ピリジン環側に置換しており、直鎖のアルキルJ&又は
アルコキシ基がフェニル核上に置換している化合物に過
ぎない。
Soc, Countries, 3rd 1979
2.1007-1.3. According to this, all of the obtained compounds have a linear alkyl 1& substituted on the pyridine ring side, and are simply compounds in which a linear alkyl J& or an alkoxy group is substituted on the phenyl nucleus.

酸素原子を介して各々の環に結合している方が。The one that is bonded to each ring via an oxygen atom.

駆動性能において優れていることが他の化合物に関する
実験から判っている。又、不斉炭素原f−の存在によっ
てカイラルスメクチックC相をとるであろうことが期待
された。しかしながら、以下の記述からも明らかになる
が、カイラルスメクチックC相はとらず、スメクチック
A相をとったに過ぎなかった。液晶化合物の構造と相と
の関係が区々であることがわかる。
Experiments with other compounds have shown that this compound has excellent drive performance. Furthermore, it was expected that a chiral smectic C phase would be formed due to the presence of the asymmetric carbon atom f-. However, as will be clear from the description below, the chiral smectic C phase was not formed, but only the smectic A phase was formed. It can be seen that the relationship between the structure and phase of liquid crystal compounds is different.

(発明が解決しようとする問題点) 本発明の目的は、強誘電性カイラルスメクチック液晶と
ブレンドでき、それによって全体として均一化されたド
メインを得、且つ、カイラルスメクチックC相をとる温
度範囲を広くすることができる性能を有する化合物を提
供することにある。
(Problems to be Solved by the Invention) An object of the present invention is to be able to blend with a ferroelectric chiral smectic liquid crystal, thereby obtaining homogeneous domains as a whole, and widening the temperature range in which the chiral smectic C phase takes place. The objective is to provide a compound that has the ability to

(問題点を解決するだめの手段) 本発明化合物は次のようにして合成される。(Failure to solve the problem) The compound of the present invention is synthesized as follows.

即ち、 (W) (式中Rは分子鎖中に不斉炭素原子をもつ光学的に活性
なアルキル基、kは直鎖状アルキル基、Xはハロゲン原
子、Aはハロゲン原子又はスルホン式(I)で示される
5−(4’−ハイドロキシフェニル)ビリジノン−2を
、ジエチルアニリン、ジメチルアニリン、1−リエチル
アミン、ピリジンなどの塩基性化合物の存在下、溶媒の
存在又は不存在で、オキシ塩化燐、三塩化燐、三臭化燐
、五塩化燐、塩化チオニルなどのハロゲン化剤と反応さ
せ式(■)で示される化合物を得る。(反応1)得られ
た式(II)で示される化合物を、ジメチルホルムアミ
ド、アセトアミド、トルエン、キシレン、テトラヒドロ
フラン、ジオキサン、ジメチルスルホキシド、ジグリム
などの適宜溶媒中、R−O−Mで示されるアルキルオキ
シアルカリ金属塩と反応させる。ここにおいてアルキル
オキシとしては、ブチルオキシ、ペンチルオキシ、ヘキ
シルオキシ、ヘプチルオキシ、オクチルオキシ、ノニル
オキシ、デシルオキシ、ウンデシルオキシ。
That is, (W) (wherein R is an optically active alkyl group having an asymmetric carbon atom in the molecular chain, k is a linear alkyl group, X is a halogen atom, A is a halogen atom or a sulfone formula (I ) in the presence of a basic compound such as diethylaniline, dimethylaniline, 1-ethylamine, or pyridine, in the presence or absence of a solvent, to phosphorus oxychloride. , react with a halogenating agent such as phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, or thionyl chloride to obtain a compound represented by formula (■). (Reaction 1) Obtained compound represented by formula (II) is reacted with an alkyloxy alkali metal salt represented by R-O-M in an appropriate solvent such as dimethylformamide, acetamide, toluene, xylene, tetrahydrofuran, dioxane, dimethylsulfoxide, diglyme, etc. Here, alkyloxy is butyloxy. , pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy.

ドデシルオキシなどの直鎖状アルキルオキシが挙げられ
、アルカリ金属としてはす1−リウム、カリウムなどで
ある。かくて1式(Ill)で示される化合物を得る。
Examples include linear alkyloxy such as dodecyloxy, and alkali metals include 1-lium, potassium, and the like. In this way, a compound represented by formula 1 (Ill) is obtained.

(反応2) 得られた式(n[)で示される化合物を、適宜溶媒中、
ナトリウム、カリウムなどのアルカリ金属又は、炭酸カ
リウム、炭酸ソーダ、水素化ナトリラム、ナトリウムア
ミド、カリウムアミドなどのアルカリ金属塩の共存下、
分子鎖中に不斉炭素原子を有する光学活性なアルキルハ
ライド、例えば。
(Reaction 2) The obtained compound represented by formula (n[) is mixed in an appropriate solvent,
In the coexistence of an alkali metal such as sodium or potassium or an alkali metal salt such as potassium carbonate, soda carbonate, sodium hydride, sodium amide, potassium amide, etc.
Optically active alkyl halides having asymmetric carbon atoms in the molecular chain, for example.

(S)−2−メチルブチルクロリド、(S) −2−メ
チルブチルプロミド、(S)−3−メチルペンチルクロ
リド、(S)−4−メチルへキシルク〆ロリド、(S)
−5−メチルへブチルクロリド。
(S)-2-methylbutyl chloride, (S)-2-methylbutyl bromide, (S)-3-methylpentyl chloride, (S)-4-methylhexyl chloride, (S)
-5-Methylhebutyl chloride.

(S)−6−メチルオクチルクロリドなどを、あるいは
、光学活性なアルキルスルホン酸エステル例えば(S)
−2−メチルブチルP−トルエンスルホネート、(S)
−3−メチルペンチルp−トルエンスルホネート、(S
)−4−メチルヘキシルI】−トルエンスルホネート、
(S)−5−メチルオクチルp−トルエンスルホネート
、(S)−6−メチルオクチルp−トルエンスルホネー
トなどを反応させ、式(TV)で示される化合物を得る
(S)-6-methyloctyl chloride, etc., or an optically active alkyl sulfonic acid ester such as (S)
-2-Methylbutyl P-toluenesulfonate, (S)
-3-methylpentyl p-toluenesulfonate, (S
)-4-methylhexyl I]-toluenesulfonate,
(S)-5-methyloctyl p-toluenesulfonate, (S)-6-methyloctyl p-toluenesulfonate, etc. are reacted to obtain a compound represented by formula (TV).

反応2で用いられた溶媒が好適に使用される。The solvent used in reaction 2 is preferably used.

(反応3) 更にまた1本発明化合物は別の方法で造ることもできる
。即ち、式(1)で示されろ化合物を反応3と同様にし
て式(V)で示される化合物を11)る。(反応4) 1;)られた式(V)で示される化合物を反応]−と同
様にして式(VI)で示される化合物を得る。
(Reaction 3) Furthermore, a compound of the present invention can also be produced by another method. That is, the compound represented by formula (1) is converted to a compound represented by formula (V) in the same manner as in reaction 3 (11). (Reaction 4) A compound represented by formula (VI) is obtained in the same manner as in 1;).

(反応5) 得られた式(VI)で示される化合物を反応2と同様に
して式(rV)で示される化合物を得る。
(Reaction 5) The obtained compound represented by formula (VI) is treated in the same manner as in reaction 2 to obtain a compound represented by formula (rV).

(反応6) 憂 RとRが相互に入れ替わった化合物は1反応2と反応3
において使用する原料を交換して1反応させることによ
って造られる。反応4と反応6も同様である。
(Reaction 6) Compounds in which R and R are interchanged are Reaction 2 and Reaction 3.
It is produced by exchanging the raw materials used in 1 and performing one reaction. The same applies to reactions 4 and 6.

かくて本発明化合物は、本出願人らの出願に係るフェニ
ルピリミジン系強誘電性カイラルスメクチック化合物と
ブレンドされると、均一性の良いドメインを与える。即
ち、電低光学素子に使用するとシャープなコントラス1
−を与えることが判った。同時にまた。フェニルピリミ
ジン系強誘電性カイラルスメクチック化合物の結晶化温
度をより低温側へ下げ、結果としてカイラルスメクチッ
クC相の温度範囲を拡大する働きをすることが判った。
Thus, when the compound of the present invention is blended with the phenylpyrimidine-based ferroelectric chiral smectic compound of the applicant's application, it provides domains with good uniformity. In other words, when used in low voltage optical elements, sharp contrast 1
It was found that -. At the same time again. It has been found that the crystallization temperature of a phenylpyrimidine-based ferroelectric chiral smectic compound is lowered to a lower temperature, and as a result, the temperature range of the chiral smectic C phase is expanded.

ここにおいて、フェニルピリミジン系強誘電性カイラル
スメクチック化合物としては、特願昭59−21.53
67、同59−141700、I’i’1159−11
7209、同59−14402.同59−250171
、同60−4211.6、同6o−42117、同60
−56652に明らかにされている。
Here, as the phenylpyrimidine-based ferroelectric chiral smectic compound, Japanese Patent Application No. 59-21.53
67, 59-141700, I'i'1159-11
7209, 59-14402. 59-250171
, 60-4211.6, 6o-42117, 60
-56652.

以下、実施例を記述して更に本発明を詳述する。Hereinafter, the present invention will be further explained in detail by describing examples.

実施例\ (1)2−クロロ−5−(4’−ハイドロキシフェニル
)ピリジンの合成: 5−(4’−ハイドロキシフェニル)ビリジノン−2を
2.0g、オキシ塩化燐10m1及びジエチルアニリン
1.5mlを加えて、15時間還流した。反応後、過剰
のオキシ塩化燐を留去し、残渣を氷水で分解した。析出
結晶を濾取し、乾燥して2.21gの2−クロロ−5−
(4’−ハイドロキシフェニル)ピリジンを得た。
Example (1) Synthesis of 2-chloro-5-(4'-hydroxyphenyl)pyridine: 2.0 g of 5-(4'-hydroxyphenyl)pyridinone-2, 10 ml of phosphorus oxychloride, and 1.5 ml of diethylaniline. was added and refluxed for 15 hours. After the reaction, excess phosphorus oxychloride was distilled off, and the residue was decomposed with ice water. The precipitated crystals were collected by filtration and dried to give 2.21 g of 2-chloro-5-
(4'-hydroxyphenyl)pyridine was obtained.

IRy’  (c;):1610.1520.1235
、 980.825 →←謄→−具 (2)  5− (4’−ハイドロキシフェニル)−2
−ウンデシロキシピリジンの合成: 300m1ナスフラスコに50%水素化ナトリウム4.
2g (0,088mo 1)、f、燥したジメチルホ
ルムアミド160 m l及びローウンデシルアルコー
ル15.ogを入れ、室温で約1時間攪拌後、2−クロ
ロ−5−(4−ハイドロキシフェニル)ピリジン9.0
gを加え、80℃で8時間攪拌を行った。反応終了後、
氷水に注ぎ、酢酸エチルで抽出し、5%水酸化カリウム
水溶液100m1で洗浄し、硫酸マグネシウムで乾燥後
、溶媒を留去した。残渣をシリカゲルカラムクロマトグ
ラフィーで精製し5題記化合物0.62gを得た。
IRy'(c;): 1610.1520.1235
, 980.825 →←transfer→-tool (2) 5- (4'-hydroxyphenyl)-2
-Synthesis of undecyloxypyridine: 4. 50% sodium hydride in a 300ml eggplant flask.
2 g (0,088 mo 1), f, 160 ml dry dimethylformamide and raw undecyl alcohol 15. After stirring at room temperature for about 1 hour, 9.0% of 2-chloro-5-(4-hydroxyphenyl)pyridine was added.
g was added thereto, and the mixture was stirred at 80°C for 8 hours. After the reaction is complete,
The mixture was poured into ice water, extracted with ethyl acetate, washed with 100 ml of a 5% aqueous potassium hydroxide solution, dried over magnesium sulfate, and then the solvent was distilled off. The residue was purified by silica gel column chromatography to obtain 0.62 g of the title compound 5.

IR^、、(cil) : 3300〜2600.16
15.1590.1120.84O NMR(60MIIz、CDC1,)δ (pp−) 
:0.6−2.0  (m、  21H)3.63  
   (t、2H) 6.7−7、 9  (m、  6H)8.5    
    (d、  LH)門8丹+−一 (、、E)(S)−5−[4’−(2−メチルブチルオ
キシ)フェニル]−2−n−ウンデシルオキシピリジン
の合成: 50m1ナスフラスコに50%水素化ナトリウム0.0
4g (0,OO085mo 1)、乾燥ジメチルホル
ムアミド10m1及び5−(4’−ハイドロキシフェニ
ル)−2−n−ウンデシルオキシピリジン0.25g 
(0,OO076mol)を入れ、80℃で1時間攪拌
後、(S)−2−メチルブチルP−トルエンスルホネー
ト0.19g(0,00079mo l)を乾燥ジメチ
ルホルムアミド2mlに溶かして加え、80℃で10時
間攪拌した。反応終了後、氷水にあけ、酢酸エチルで抽
出(50mlX3) し、5%水酸化ナトリウム水溶液
(50mlX3)、飽和食塩水(100mlX4)で順
に洗浄し、硫酸マグ不ソウムで乾燥後のち、)8媒を留
去して緑色油状物0.28gを得た。これを薄層クロマ
[グラフィ=(MERCK、S+LICAGEI、 6
0.1−25411で分離精製し、題記化合物0.2g
を得た。
IR^,, (cil): 3300-2600.16
15.1590.1120.84O NMR (60MIIz, CDC1,) δ (pp-)
:0.6-2.0 (m, 21H) 3.63
(t, 2H) 6.7-7, 9 (m, 6H) 8.5
(d, LH) Synthesis of gate 8tan+-1(,,E)(S)-5-[4'-(2-methylbutyloxy)phenyl]-2-n-undecyloxypyridine: 50ml eggplant flask 50% sodium hydride 0.0
4g (0,OO085mo 1), 10ml of dry dimethylformamide and 0.25g of 5-(4'-hydroxyphenyl)-2-n-undecyloxypyridine
(0,OO076 mol) and stirred at 80°C for 1 hour, then added 0.19 g (0,00079 mol) of (S)-2-methylbutyl P-toluenesulfonate dissolved in 2 ml of dry dimethylformamide, and stirred at 80°C for 1 hour. Stir for hours. After the reaction is complete, pour into ice water, extract with ethyl acetate (50 ml x 3), wash sequentially with 5% sodium hydroxide aqueous solution (50 ml x 3) and saturated brine (100 ml x 4), dry over magnesium sulfate, and extract with ethyl acetate (50 ml x 3). was distilled off to obtain 0.28 g of a green oil. This is thin layer chroma [graphie=(MERCK, S+LICAGEI, 6
Separation and purification of 0.1-25411 yielded 0.2 g of the title compound.
I got it.

I R(nu j o I)i)max (cm−’)
:1 G 10.1490.1470.1380,12
55.82ONMR(CDCl2 ) δ(ppm):
0.6〜2.3 (m、30H) 3.77     (d、28) 4.27     (t、2H) 6.68     (a、IH) 6.88     (d、2H) 7.35     (m、3H) 7.63     (t、IH) 8.23     (d、IH) 得られた題記化合物は、下のような転移温度を示した。
I R(nu j o I)i)max (cm-')
:1 G 10.1490.1470.1380,12
55.82ONMR (CDCl2) δ (ppm):
0.6-2.3 (m, 30H) 3.77 (d, 28) 4.27 (t, 2H) 6.68 (a, IH) 6.88 (d, 2H) 7.35 (m, 3H) 7.63 (t, IH) 8.23 (d, IH) The obtained title compound showed the following transition temperature.

また、2の化合物を下に示した比率でピリミジン系液晶
組成物とブレンドし、転移温度を見た。
In addition, compound No. 2 was blended with a pyrimidine-based liquid crystal composition in the ratio shown below, and the transition temperature was observed.

CzLCHCHzOGQOC+ +Hzz−ri   
 25重量%?H′ CzHsCH(C)Iz)sOGfiOcsLt−n 
  3o重量%−3,2’C ところで、上記組成のピリミジン系液晶化合物3種のみ
の転移温度は、 141Cフ4.9’0   フe、o’cCry   
 Sc”    S、    +5゜10’Q であり、実施例の化合物を2のピリミジン系液晶組成物
にブレンドすることにより、液晶からSc“相への転移
温度を大きく下げることが出来る。
CzLCHCHzOGQOC+ +Hzz-ri
25% by weight? H' CzHsCH(C)Iz)sOGfiOcsLt-n
3o wt % - 3,2'C By the way, the transition temperature of only the three types of pyrimidine liquid crystal compounds having the above composition is 141C f4.9'0 f e, o'cCry
Sc''S, +5°10'Q, and by blending the compound of Example into the pyrimidine liquid crystal composition of 2, the transition temperature from liquid crystal to Sc'' phase can be significantly lowered.

参考例 イ)3−シアノ−5−(4’−ハイドロキシフェニル)
ビリジノン−2の合成: 1−ジメチルアミツー:’−(4’−ハイドロキシフェ
ニル)−3−ジメチルアミノプロペン−1過塩素酸塩(
このものはH,Zaschke、S。
Reference example a) 3-cyano-5-(4'-hydroxyphenyl)
Synthesis of pyridinone-2: 1-dimethylamitsu:'-(4'-hydroxyphenyl)-3-dimethylaminopropene-1 perchlorate (
This one is by H. Zaschke, S.

Arndt、V、Wagnsr、H,5chubart
  Z、Cham、17 293 294(1977)
の方法により合成した。)3.2gと2−シアノアセト
アミド0.84gを乾燥エタノール20m1に懸濁し、
28%ソジウムメチラートメタノール溶液588gを加
え、6時間還流下に反応を行った0反応液を氷水に注ぎ
、希塩酸で酸性として析出結晶を濾取した。水洗後、乾
燥して題記化合物1.98gを得た。
Arndt, V., Wagner, H., 5chubart.
Z, Cham, 17 293 294 (1977)
It was synthesized by the method of ) and 0.84 g of 2-cyanoacetamide were suspended in 20 ml of dry ethanol,
588 g of 28% sodium methylate methanol solution was added and the reaction was carried out under reflux for 6 hours. The reaction solution was poured into ice water, acidified with dilute hydrochloric acid, and the precipitated crystals were collected by filtration. After washing with water and drying, 1.98 g of the title compound was obtained.

IH久、、(cm−’):3350,3300,224
0.1670..1530.1280.11850)5
−(4’−ハイドロキシフェニル)とリジノン−2の合
成: 5gの3−シアノ−5−(4’−ハイドロキシフェニル
)ビリジノン−2に85%tjJ&50m+を加えて3
1時間加熱還流した後、反応液を氷水に注ぎ、析出結晶
を濾取、水洗、乾燥して題記化合物4.69gを得た。
IH Ku,, (cm-'): 3350, 3300, 224
0.1670. .. 1530.1280.11850)5
Synthesis of -(4'-hydroxyphenyl) and lysinone-2: Add 85% tjJ & 50m+ to 5 g of 3-cyano-5-(4'-hydroxyphenyl)pyridinone-2 and prepare 3
After heating under reflux for 1 hour, the reaction solution was poured into ice water, and the precipitated crystals were collected by filtration, washed with water, and dried to obtain 4.69 g of the title compound.

■RV)、、、(c+m−’):3300〜2400.
 1670.1630,1525.1280.835以
■RV),,,(c+m-'): 3300-2400.
1670.1630, 1525.1280.835 or higher

Claims (1)

【特許請求の範囲】 式 ▲数式、化学式、表等があります▼ (式中R^*は分子鎖中に不斉炭素原子を有する光学的
に活性なアルキル基を、Rは直鎖状アルキル基を示す。 これらは相互に入れ替わっていてもよい。) で示されるフェニルピリジン誘導体
[Claims] Formulas include mathematical formulas, chemical formulas, tables, etc. (These may be interchanged.) Phenylpyridine derivatives represented by
JP61080726A 1986-04-08 1986-04-08 Phenyl pyridine derivative Expired - Fee Related JPH0692370B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP61080726A JPH0692370B2 (en) 1986-04-08 1986-04-08 Phenyl pyridine derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP61080726A JPH0692370B2 (en) 1986-04-08 1986-04-08 Phenyl pyridine derivative

Publications (2)

Publication Number Publication Date
JPS62238265A true JPS62238265A (en) 1987-10-19
JPH0692370B2 JPH0692370B2 (en) 1994-11-16

Family

ID=13726369

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Country Status (1)

Country Link
JP (1) JPH0692370B2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4898455A (en) * 1986-04-22 1990-02-06 Hoffmann-La Roche Inc. Pyridine liquid crystalline compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4898455A (en) * 1986-04-22 1990-02-06 Hoffmann-La Roche Inc. Pyridine liquid crystalline compounds

Also Published As

Publication number Publication date
JPH0692370B2 (en) 1994-11-16

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