JPH03227973A - Preparation of quinoline-5-sulfonic acid - Google Patents
Preparation of quinoline-5-sulfonic acidInfo
- Publication number
- JPH03227973A JPH03227973A JP2169190A JP2169190A JPH03227973A JP H03227973 A JPH03227973 A JP H03227973A JP 2169190 A JP2169190 A JP 2169190A JP 2169190 A JP2169190 A JP 2169190A JP H03227973 A JPH03227973 A JP H03227973A
- Authority
- JP
- Japan
- Prior art keywords
- quinoline
- sulfur trioxide
- sulfonic acid
- solvent
- compound
- 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
- KVGSJGNWRDPVKA-UHFFFAOYSA-N quinoline-5-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=N1 KVGSJGNWRDPVKA-UHFFFAOYSA-N 0.000 title claims abstract description 22
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 36
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 239000011280 coal tar Substances 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract description 2
- 239000000049 pigment Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 239000011269 tar Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- -1 aliphatic halogenated hydrocarbons Chemical class 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000004811 liquid chromatography Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- YYFLDZZDOUDZQM-UHFFFAOYSA-N 3-[1-[[4-(3-phenylquinolin-2-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 YYFLDZZDOUDZQM-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- VHFUHRXYRYWELT-UHFFFAOYSA-N methyl 2,2,2-trichloroacetate Chemical compound COC(=O)C(Cl)(Cl)Cl VHFUHRXYRYWELT-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- FBNVOSBSLQPUBQ-UHFFFAOYSA-N quinolin-1-ium-7-sulfonate Chemical compound C1=CC=NC2=CC(S(=O)(=O)O)=CC=C21 FBNVOSBSLQPUBQ-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は農薬あるいは染顔料等の原料となる工業的に有
用な物質であるキノリン−５−スルホン酸の製造方法に
関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a method for producing quinoline-5-sulfonic acid, which is an industrially useful substance used as a raw material for agricultural chemicals, dyes and pigments, and the like.
〈従来の技術〉
殻に、キノリン−５−スルホン酸は、ｍアミノベンゼン
スルホン酸、グリセリンおよび硫酸とをニトロベンゼン
等の酸化剤の存在下で加熱することにより製造される（
Ｊ、Ｃｈｅｍ、５ｏｃ１９４７．４３７．）。 しかし
、本製造法では、副生成物として、キノリン−５−スル
ホン酸とほぼ同量のキノリン−７−スルホン酸が生成し
、かつ両者を合わせた収率が５１，５モル％（ｍ−アミ
ノベンゼンスルホン酸基準）と極めて低く、経済的に高
収率でキノリン−５−スルホン酸を製造する事が極めて
困難であった。<Prior Art> In the shell, quinoline-5-sulfonic acid is produced by heating m-aminobenzenesulfonic acid, glycerin and sulfuric acid in the presence of an oxidizing agent such as nitrobenzene (
J, Chem, 5oc1947.437. ). However, in this production method, almost the same amount of quinoline-7-sulfonic acid as quinoline-5-sulfonic acid is produced as a by-product, and the combined yield of both is 51.5 mol% (m-amino It was extremely difficult to economically produce quinoline-5-sulfonic acid with a high yield.
〈発明が解決しようとする課題〉
そこで、本発明は、前記従来技術の問題点を解決し、経
済的に、かつ高収率でキノリン−５＝スルホン酸を製造
する技術を提供することを目的とする。<Problems to be Solved by the Invention> Therefore, the purpose of the present invention is to solve the problems of the prior art and provide a technology for producing quinoline-5=sulfonic acid economically and in high yield. shall be.
く課題を解決するための手段〉
上記課題を解決するために、本発明者らはキノリンを三
酸化イオウでスルホン化することにより、高収率でキノ
リン−５−スルホン酸を製造できる事を見い出し本発明
に至った。Means for Solving the Problems In order to solve the above problems, the present inventors discovered that quinoline-5-sulfonic acid can be produced in high yield by sulfonating quinoline with sulfur trioxide. This led to the present invention.
すなわち、本発明は、キノリンを三酸化イオウでスルホ
ン化することを特徴とするキノリン−５−スルホン酸の
製造方法を提供するものである。That is, the present invention provides a method for producing quinoline-5-sulfonic acid, which is characterized by sulfonating quinoline with sulfur trioxide.
以下、本発明について詳細に説明する。The present invention will be explained in detail below.
本発明で用いる出発原料のキノリンは、コールタールか
ら製造されるタール塩基油を蒸留することにより、また
は合成法により得られるが、特に限定はしない。The starting material quinoline used in the present invention can be obtained by distilling tar base oil produced from coal tar or by a synthetic method, but is not particularly limited.
本発明に使用する三酸化イオウはα、βおよびγ態のい
ずれも用いることができるが、取扱上の利便性からγ態
を用いるほうが好ましい。The sulfur trioxide used in the present invention can be used in any of the α, β and γ forms, but it is preferable to use the γ form for convenience in handling.
またこれらは気体、液体、固体のいずれの状態で使用し
てもよい。Further, these may be used in any state of gas, liquid, or solid.
三酸化イオウの使用量はキノリンに対して１倍モル〜８
倍モル、より好ましくは２倍モル〜６倍モルである。
１倍モル以下の使用量では化学量論的に不足しキノリ
ン−５−スルホン酸の収率が低く、８倍モル以上使用し
てもキノリン−５−スルホン酸の収率は向上せず経済的
ではない。The amount of sulfur trioxide used is 1 to 8 moles relative to quinoline.
It is twice the mole, more preferably 2 times the mole to 6 times the mole.
If the amount used is less than 1 times the mole, it will be stoichiometrically insufficient and the yield of quinoline-5-sulfonic acid will be low, and if it is used more than 8 times the mole, the yield of quinoline-5-sulfonic acid will not improve and it is not economical. isn't it.
反応温度は一２０〜２６０℃、好ましくは４０〜２００
℃の範囲である。 反応時間は酸化イオウ使用量、反応
温度などにもよるのて概には言えないが、好ましくは１
０分以上がよい。The reaction temperature is -20 to 260°C, preferably 40 to 200°C.
℃ range. The reaction time cannot be generalized as it depends on the amount of sulfur oxide used, the reaction temperature, etc., but it is preferably 1
0 minutes or more is better.
キノリンおよび三酸化イオウはそのまま混合して反応さ
せてもよいし、キノリンおよび／または三酸化イオウを
これらに不活性または実質的に不活性な溶媒に懸濁ある
いは溶解した後反応させてもよい。The quinoline and sulfur trioxide may be mixed as they are and reacted, or the quinoline and/or sulfur trioxide may be suspended or dissolved in an inert or substantially inert solvent and then reacted.
溶媒としては、塩化メチレン、クロロポルム、四塩化炭
素、トリクロロフロルメタン等の脂肪族ハロゲン化炭化
水素、二酸化イオウ、塩化スルホニル、二硫化炭素等の
イオウ化合物、ギ酸メチル、酢酸メチル、トリクロロ酢
酸メチル等の低級脂肪酸エステル、さらにはニトロメタ
ン等から選ばれる１種又は２種以上の混合溶媒が使用可
能である。Examples of solvents include aliphatic halogenated hydrocarbons such as methylene chloride, chloroporm, carbon tetrachloride, and trichlorofluoromethane, sulfur compounds such as sulfur dioxide, sulfonyl chloride, and carbon disulfide, methyl formate, methyl acetate, and methyl trichloroacetate. One or more mixed solvents selected from lower fatty acid esters, nitromethane, etc. can be used.
溶媒使用量はキノリンおよび三酸化イオウに対して１０
重量倍以下が好ましい。 １０重量倍以上の使用量で
は反応器が大きくなり、かつ溶媒を回収するために多大
なエネルギーを要し、経済的ではない。The amount of solvent used is 10% for quinoline and sulfur trioxide.
It is preferably less than twice the weight. If the amount used is 10 times the weight or more, the reactor will become large and a large amount of energy will be required to recover the solvent, which is not economical.
反応終了後、反応生成物中の過剰の三酸化イオウあるい
は三酸化イオウと溶媒を加熱蒸発あるいは乾燥空気等を
流通させ除去して、反応生成物を回収してもよいし、反
応生成物を水中に注いだ後ライミングソーデーション法
あるいは硫酸とオキソニウム化合物を作るエーテル、エ
ステル、ケトン類等の溶媒を添加して回収してもよい。After the reaction is completed, the excess sulfur trioxide or sulfur trioxide and solvent in the reaction product may be removed by heating and evaporation or by passing dry air, etc., and the reaction product may be recovered. Alternatively, the reaction product may be recovered in water. The solution may be recovered by liming sodation or by adding sulfuric acid and a solvent such as ether, ester, or ketone that forms an oxonium compound.
反応生成物中のキノリン−５−スルホン酸の純度をさら
に向上させるために、水、アルコール類を使用して再結
晶精製することにより、さらに高純度のキノリン−５−
スルホン酸が得られる。In order to further improve the purity of quinoline-5-sulfonic acid in the reaction product, even higher purity quinoline-5-
Sulfonic acid is obtained.
〈実施例〉 以下、本発明を実施例に基づき具体的に説明する。<Example> Hereinafter, the present invention will be specifically explained based on Examples.
（実施例１）
キノリン１２．９ｇに液体三酸化イ才つ１６、Ｏｇを反
応温度が４０℃を超えないように滴下した。 滴下終了
後１５０℃まで昇温し２時間反応させた。 反応終了後
反応系内に乾燥空気を導入し過剰の三酸化イオウを除去
した。 反応生成物が２０．５ｇ得られた。 液体クロ
マトグラフ法で測定したキノリン−５スルホン酸の純度
は８２．０％であり、キノリン−５−スルホン酸の収率
は８０．４モル％（キノリン基準）であフた。(Example 1) 16.0 g of liquid trioxide was added dropwise to 12.9 g of quinoline so that the reaction temperature did not exceed 40°C. After the dropwise addition was completed, the temperature was raised to 150°C and the mixture was reacted for 2 hours. After the reaction was completed, dry air was introduced into the reaction system to remove excess sulfur trioxide. 20.5 g of reaction product was obtained. The purity of quinoline-5-sulfonic acid measured by liquid chromatography was 82.0%, and the yield of quinoline-5-sulfonic acid was 80.4 mol% (based on quinoline).
これを水−メタノールの混合溶媒で再結晶精製したとこ
ろ、１５．９ｇの結晶が得られた。When this was recrystallized and purified using a mixed solvent of water and methanol, 15.9 g of crystals were obtained.
液体クロマトグラフ法で測定したキノリン５−スルホン
酸の純度は９９．５％であり、スルホン化、再結晶の両
工程を合わせたキノリン−５−スルホン酸の総合収率は
、７５．７モル％（キノリン基準）であった。The purity of quinoline-5-sulfonic acid measured by liquid chromatography is 99.5%, and the total yield of quinoline-5-sulfonic acid including both sulfonation and recrystallization steps is 75.7 mol%. (quinoline standard).
（実施例２）
キノリン１２．９ｇを四塩化炭素５０ｇに溶解した後、
液体三酸化イオウ２４０ｇを反応温度か４０℃を超えな
いように滴下した。 滴下終了後７６℃まで昇温し２時
間反応させた。(Example 2) After dissolving 12.9 g of quinoline in 50 g of carbon tetrachloride,
240 g of liquid sulfur trioxide was added dropwise so that the reaction temperature did not exceed 40°C. After the dropwise addition was completed, the temperature was raised to 76°C and the mixture was reacted for 2 hours.
反応終了後反応生成物を水１０ｇに注いた。After the reaction was completed, the reaction product was poured into 10 g of water.
その後攪拌しなからメチルイソブチルケ（・ン５００ｇ
を加え３０分攪拌した。 攪拌終了後析出した結晶を吸
引が過て回収し、真空乾燥で結晶に付着している溶媒を
除去した。 この結果、１５０ｇの結晶が得られた。
液体クロマトグラフ法で測定したキノリン−５−スルポ
ン酸の純度は７８．０％であり、キノリン−５スルホン
酸の収率は５６０モル％（キノリン基準）てあった。After that, without stirring, 500 g of methyl isobutyl
was added and stirred for 30 minutes. After the stirring was completed, the precipitated crystals were collected by suction, and the solvent adhering to the crystals was removed by vacuum drying. As a result, 150 g of crystals were obtained.
The purity of quinoline-5-sulfonic acid measured by liquid chromatography was 78.0%, and the yield of quinoline-5-sulfonic acid was 560 mol% (based on quinoline).
（比較例１）
文献（Ｊ、Ｃｈｅｍ、Ｓｏｃ、、１９４７．４３７．）
の追試を行なった。(Comparative Example 1) Literature (J, Chem, Soc, 1947.437.)
A follow-up test was conducted.
ｍ−アミノヘンゼンスルホン酸１００ｇ、グリセリン１
３．３ｇ、７０ｗｔ％硫酸４３３ＣＣおよびニトロベン
ゼン１１７ｇを混合し２．１３７〜１４８℃で３時間反
応させた。m-aminohenzenesulfonic acid 100g, glycerin 1
3.3 g of 70 wt % sulfuric acid 433 CC and 117 g of nitrobenzene were mixed and reacted at 2.137 to 148° C. for 3 hours.
反応終了後２００ｇの水を加え、水蒸気蒸留てニトロベ
ンゼンを除去した。 除去後、水に懸濁させた水酸化カ
ルシウムを加え、硫酸を硫酸カルシウムに変換し炉別し
た。 さらに反応生成物を濃縮し、粘着性の化合物３７
７ｇを得た。 液体クロマトグラフ法で測定したキノリ
ン−５−スルホン酸の純度は４８．０％であり、キノリ
ン−５−スルホン酸の収率は１５．０モル％（ｍ−アミ
ノベンゼンスルホン酸基準）であった。After the reaction was completed, 200 g of water was added and nitrobenzene was removed by steam distillation. After removal, calcium hydroxide suspended in water was added to convert the sulfuric acid into calcium sulfate, which was then separated in a furnace. Further, the reaction product was concentrated to form a sticky compound 37.
7g was obtained. The purity of quinoline-5-sulfonic acid measured by liquid chromatography was 48.0%, and the yield of quinoline-5-sulfonic acid was 15.0 mol% (based on m-aminobenzenesulfonic acid). .
〈発明の効果〉
本発明法によれは、キノリン−５−スルポン酸の収率か
高く。 かつ純度も高いため工業的に極めて有利である
。<Effects of the Invention> The method of the present invention provides a high yield of quinoline-5-sulfonic acid. In addition, it has high purity, making it extremely advantageous industrially.
Claims (1)
特徴とするキノリン−５−スルホン酸の製造方法。(1) A method for producing quinoline-5-sulfonic acid, which comprises sulfonating quinoline with sulfur trioxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2169190A JPH03227973A (en) | 1990-01-31 | 1990-01-31 | Preparation of quinoline-5-sulfonic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2169190A JPH03227973A (en) | 1990-01-31 | 1990-01-31 | Preparation of quinoline-5-sulfonic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03227973A true JPH03227973A (en) | 1991-10-08 |
Family
ID=12062095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2169190A Pending JPH03227973A (en) | 1990-01-31 | 1990-01-31 | Preparation of quinoline-5-sulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03227973A (en) |
-
1990
- 1990-01-31 JP JP2169190A patent/JPH03227973A/en active Pending
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