JPS632550B2 - - Google Patents
Info
- Publication number
- JPS632550B2 JPS632550B2 JP23076982A JP23076982A JPS632550B2 JP S632550 B2 JPS632550 B2 JP S632550B2 JP 23076982 A JP23076982 A JP 23076982A JP 23076982 A JP23076982 A JP 23076982A JP S632550 B2 JPS632550 B2 JP S632550B2
- Authority
- JP
- Japan
- Prior art keywords
- copper
- methoxy
- methoxypyridine
- methylaminopyridine
- methylamine
- 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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 22
- GXHQLRBOZRJHPZ-UHFFFAOYSA-N 6-methoxy-n-methylpyridin-2-amine Chemical compound CNC1=CC=CC(OC)=N1 GXHQLRBOZRJHPZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000005749 Copper compound Substances 0.000 claims description 8
- 150000001880 copper compounds Chemical class 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 241001076438 Oxya japonica Species 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VAVGOGHLNAJECD-UHFFFAOYSA-N 2-chloro-6-methoxypyridine Chemical compound COC1=CC=CC(Cl)=N1 VAVGOGHLNAJECD-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- -1 inorganic acid salts Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- KMODISUYWZPVGV-UHFFFAOYSA-N 2-bromo-6-methoxypyridine Chemical compound COC1=CC=CC(Br)=N1 KMODISUYWZPVGV-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 235000005324 Typha latifolia Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 244000118869 coast club rush Species 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 229940120693 copper naphthenate Drugs 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- INFPIPCTRVDPJG-UHFFFAOYSA-N o-naphthalen-2-yl chloromethanethioate Chemical compound C1=CC=CC2=CC(OC(=S)Cl)=CC=C21 INFPIPCTRVDPJG-UHFFFAOYSA-N 0.000 description 1
- LMQJRYKENGECRN-UHFFFAOYSA-N o-naphthalen-2-yl n-(6-methoxypyridin-2-yl)-n-methylcarbamothioate Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C3C=CC=CC3=CC=2)=N1 LMQJRYKENGECRN-UHFFFAOYSA-N 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、２−メトキシ−６−メチルアミノピ
リジンの製造法に関する。
２−メトキシ−６−メチルアミノピリジンは、
医薬、濃薬等の中間体として有用な化合物であ
る。
本発明者らは、既に２−ハロ−６−メトキシピ
リジンとメチルアミンとの反応によりこれを製造
する方法を提案した。
更に、本発明者らは種々の試験をし鋭意検討し
た結果２−ハロ−６−メトキシピリジンを銅或い
は銅化合物の存在下メチルアミンと反応させるこ
とにより副生成物の生成を抑制し、高収率で２−
メトキシ−６−メチルアミノピリジンを製造でき
ることを見い出し本発明を完成した。本発明は一
般式
The present invention relates to a method for producing 2-methoxy-6-methylaminopyridine. 2-methoxy-6-methylaminopyridine is
It is a compound useful as an intermediate for pharmaceuticals, concentrated drugs, etc. The present inventors have already proposed a method for producing this by reacting 2-halo-6-methoxypyridine with methylamine. Furthermore, as a result of various tests and intensive studies, the present inventors have found that by reacting 2-halo-6-methoxypyridine with methylamine in the presence of copper or a copper compound, the formation of by-products can be suppressed and a high yield can be achieved. 2- in rate
They discovered that methoxy-6-methylaminopyridine can be produced and completed the present invention. The present invention is based on the general formula
【式】（式中Ｘは臭素原子又
は塩素原子を示す。）で表わされる２−ハロ−６
−メトキシピリジンを銅或いは、銅化合物の存在
下メチルアミンと反応させることを特徴とする２
−メトキシ−６−メチルアミノピリジンの製造法
を提供するものである。
本発明は、銅或いは、銅化合物を用いるが銅化
合物としては、硫酸銅、塩化銅、硝酸銅等の無機
酸塩、ナフテン酸銅、酢酸銅等の有機酸塩、酸化
銅等の酸化物、水酸化銅等の水酸化物等を挙げる
ことができる。そして金属銅或いは、これらの銅
化合物は、通常２−ハロ−メトキシピリジンに対
して約１ないし約50重量％好ましくは約５〜約30
重量％用いる。
メチルアミンの使用量は、２−ハロ−６−メト
キシピリジンに対し約２ないし約20倍モル、好ま
しくは約２ないし約10倍モルである。反応を円滑
に進めるために溶媒を用いることが好ましい。溶
媒としては、２−ハロ−６−メトキシピリジン、
メチルアミンと反応せず、しかもメチルアミンを
溶解する水、ベンゼン、アルコール等を挙げるこ
とができる。
メチルアミンは、常温では気体であり、通常は
水溶液として入手できる。そのため、一般には２
−ハロ−６−メトキシピリジンと銅或いは銅化合
物の存在下メチルアミン水溶液と反応させるのが
簡便である。反応温度は約80ないし約150℃、好
ましくは約100ないし約130℃であり、反応時間は
約１ないし約20時間が適当である。
本発明の方法により２−メトキシ−６−メチル
アミノピリジンを高収率で得ることができる。
次に実施例によつて本発明を詳細に説明するが
本発明は、これら実施例のみに限定されるもので
はない。
実施例 １
200mlの電磁撹拌式オートクレーブに２−クロ
ル−６−メトキシピリジン20gr、塩化第一銅4gr、
40％メチルアミン水溶液60mlを取り、120℃にて
８時間反応させた。反応終了後オートクレーブを
冷却し、開缶して反応液を取り出した。次いで反
応液中の２−メトキシ−６−メチルアミノピリジ
ンをエーテルで抽出した。エーテル抽出液を無水
硫酸マグネシウムで乾燥し、エーテルを留去し
た。
エーテル留去後の残査を減圧蒸留し、沸点88〜
92℃／５mmHgの２−メトキシ−６−メチルアミ
ノピリジン14.9grを得た。２−メトキシ−６−メ
チルアミノピリジンの収率は、２−クロル−６−
メトキシピリジン基準で77.5％であつた。
赤外線吸収スペクトル（NaCl）
3420（−NH）、2950（Ｃ−Ｈ）、1600、1475、
核磁気共鳴吸収スペクトル（CCl4、内部標準
TMS）
δ 2.86(d)ppm（3H）
δ 3.85(S)ppm（3H）
δ 4.40(d)ppm（1H）
δ 5.84(d)ppm（1H）
δ 5.94(d)ppm（1H）
δ 7.12(t)ppm（1H）
元素分析（C7H10N2Oとして）結果は以下の通
りであつた。
Ｃ Ｈ Ｎ Ｏ
分析値（％） 60.75 7.22 20.35 11.68
理論値（％） 60.85 7.30 20.27 11.58
GC−MSによる分子量 138
実施例 ２
実施例１と同一の反応装置に２−ブロモ−６−
メトキシピリジン30gr、硫酸銅（５水塩）5gr、
40％−メチルアミン水溶液60mlを取り、100℃に
て10時間反応させた。
反応終了後、実施例１と同様の実験操作を行い
２−メトキシ−６−メチルアミノピリジン16.4gr
を得た。２−メトキシ−６−メチルアミノピリジ
ンの収率は、２−ブロモ−６−メトキシピリジン
基準で74.5％であつた。
実施例 ３〜７
実施例１と同一の反応装置に２−クロル−６−
メトキシピリジン、銅或いは銅化合物、40℃−メ
チルアミン水溶液を取り表−１の反応条件にて反
応させた。
反応終了後、実施例１と同様の操作により表−
１の如き２−メトキシ−６−メチルアミノピリジ
ンを得た。2-halo-6 represented by [Formula] (wherein X represents a bromine atom or a chlorine atom)
- 2 characterized by reacting methoxypyridine with methylamine in the presence of copper or a copper compound
A method for producing -methoxy-6-methylaminopyridine is provided. In the present invention, copper or a copper compound is used. Examples of the copper compound include inorganic acid salts such as copper sulfate, copper chloride, and copper nitrate; organic acid salts such as copper naphthenate and copper acetate; oxides such as copper oxide; Examples include hydroxides such as copper hydroxide. The amount of metallic copper or copper compound thereof is usually about 1 to about 50% by weight, preferably about 5 to about 30% by weight based on 2-halo-methoxypyridine.
Use % by weight. The amount of methylamine used is about 2 to about 20 times the amount of 2-halo-6-methoxypyridine, preferably about 2 to about 10 times the amount of 2-halo-6-methoxypyridine. It is preferable to use a solvent to facilitate the reaction. As a solvent, 2-halo-6-methoxypyridine,
Examples include water, benzene, alcohol, etc., which do not react with methylamine but dissolve it. Methylamine is a gas at room temperature and is usually available as an aqueous solution. Therefore, generally 2
It is convenient to react -halo-6-methoxypyridine with an aqueous methylamine solution in the presence of copper or a copper compound. The reaction temperature is about 80 to about 150°C, preferably about 100 to about 130°C, and the reaction time is suitably about 1 to about 20 hours. By the method of the present invention, 2-methoxy-6-methylaminopyridine can be obtained in high yield. Next, the present invention will be explained in detail with reference to Examples, but the present invention is not limited to these Examples. Example 1 In a 200 ml electromagnetic stirring autoclave, 20 gr of 2-chloro-6-methoxypyridine, 4 gr of cuprous chloride,
60ml of 40% methylamine aqueous solution was taken and reacted at 120°C for 8 hours. After the reaction was completed, the autoclave was cooled, opened, and the reaction solution was taken out. Then, 2-methoxy-6-methylaminopyridine in the reaction solution was extracted with ether. The ether extract was dried over anhydrous magnesium sulfate, and the ether was distilled off. The residue after distilling off the ether is distilled under reduced pressure, and the boiling point is 88~
14.9 gr of 2-methoxy-6-methylaminopyridine was obtained at 92°C/5 mmHg. The yield of 2-methoxy-6-methylaminopyridine is 2-chloro-6-
It was 77.5% based on methoxypyridine. Infrared absorption spectrum (NaCl) 3420 (-NH), 2950 (C-H), 1600, 1475, Nuclear magnetic resonance absorption spectrum ( CCl4 , internal standard
TMS) δ 2.86(d)ppm(3H) δ 3.85(S)ppm(3H) δ 4.40(d)ppm(1H) δ 5.84(d)ppm(1H) δ 5.94(d)ppm(1H) δ 7.12( t) ppm (1H) Elemental analysis (as C 7 H 10 N 2 O) results were as follows. C H N O Analytical value (%) 60.75 7.22 20.35 11.68 Theoretical value (%) 60.85 7.30 20.27 11.58 Molecular weight by GC-MS 138 Example 2 2-Bromo-6- was added to the same reaction apparatus as Example 1.
Methoxypyridine 30gr, copper sulfate (pentahydrate) 5gr,
60 ml of 40% methylamine aqueous solution was taken and reacted at 100°C for 10 hours. After the reaction was completed, the same experimental procedure as in Example 1 was carried out to obtain 16.4 gr of 2-methoxy-6-methylaminopyridine.
I got it. The yield of 2-methoxy-6-methylaminopyridine was 74.5% based on 2-bromo-6-methoxypyridine. Examples 3 to 7 In the same reactor as Example 1, 2-chloro-6-
Methoxypyridine, copper or a copper compound, and an aqueous methylamine solution at 40°C were reacted under the reaction conditions shown in Table 1. After the reaction is completed, the table-
2-methoxy-6-methylaminopyridine as 1 was obtained.
【表】
次に本発明化合物から得られる化合物および除
草剤としての使用例を示す。
本発明の方法の目的物質である２−メトキシ−
６−メチルアミノピリジン1.38ｇ及び同量の無水
炭酸カリウムを20mlのアセトン中室温で撹拌、ア
セトン20mlに溶かしたＯ−２−ナフチル クロル
チオホルメイト2.23ｇを加え30分後反応混合物を
ベンゼンで抽出、水洗、乾燥、再結晶してＯ−２
−ナフチル Ｎ−（６−メトキシ−２−ピリジル）
−Ｎ−メチル−チオカーバメート2.75ｇを得た。
融点 95.5〜97℃
元素分析（C18H16N2O2Sとして）
Ｃ Ｈ Ｎ
分析値（％） 66.42 4.89 8.81
理論値（％） 66.65 4.97 8.64
直径９cmの磁製ポツトに水田土壌を入れ、水を
加えて代かき後、土壌表層に雑草種子を播き、２
葉期の水稲苗（品種、日本晴）を１cmの深さに、
２本２株値とした。翌日２cmの湛水を行い、Ｏ−
２−ナフチル Ｎ−（６−メトキシ−２−ピリジ
ル）−Ｎ−メチルチオカーバメート10％を含む水
和剤をポツト当り10mlの水に希釈して水面に滴下
処理した。その後、温室に静置し薬液処理３週間
後に除草効果および水稲に及ぼした影響を調査し
た。この結果、供試薬量125ｇ／10aで水稲苗に
全く薬害がなく、ノビエ、、タマガヤツリ、ホタ
ルイ、コナギ、キカシグサを100％防除した。[Table] Next, examples of compounds obtained from the compounds of the present invention and their use as herbicides are shown. 2-methoxy- which is the target substance of the method of the present invention
1.38 g of 6-methylaminopyridine and the same amount of anhydrous potassium carbonate were stirred in 20 ml of acetone at room temperature, 2.23 g of O-2-naphthyl chlorothioformate dissolved in 20 ml of acetone was added, and after 30 minutes the reaction mixture was extracted with benzene. , washed with water, dried, recrystallized to O-2
-Naphthyl N-(6-methoxy-2-pyridyl)
2.75 g of -N-methyl-thiocarbamate was obtained. Melting point 95.5-97℃ Elemental analysis (as C 18 H 16 N 2 O 2 S) C H N Analysis value (%) 66.42 4.89 8.81 Theoretical value (%) 66.65 4.97 8.64 Paddy soil was placed in a porcelain pot with a diameter of 9 cm. After adding water and plowing, weed seeds are sown on the soil surface layer.
Paddy rice seedlings (variety, Nipponbare) in the leaf stage are planted at a depth of 1 cm.
The value was set as 2 shares. The next day, the water was flooded to a depth of 2 cm, and O-
A wettable powder containing 10% of 2-naphthyl N-(6-methoxy-2-pyridyl)-N-methylthiocarbamate was diluted in 10 ml of water per pot and dropped onto the water surface. Thereafter, the plants were left in a greenhouse and three weeks after the chemical treatment, the herbicidal effect and the effect on paddy rice were investigated. As a result, there was no chemical damage to paddy rice seedlings at the amount of the test chemical of 125g/10a, and it controlled 100% of Japanese grasshopper, Japanese cyperus, bulrush, Japanese grasshopper, and Japanese grasshopper.
Claims (1)
ロ−６−メトキシピリジンを銅或いは銅化合物の
存在下メチルアミンと反応させることを特徴とす
る２−メトキシ−６−メチルアミノピリジンの製
造法。[Claims] 1. 2-halo-6-methoxypyridine represented by the general formula [Formula] (wherein X represents a bromine atom or a chlorine atom) is reacted with methylamine in the presence of copper or a copper compound. A method for producing 2-methoxy-6-methylaminopyridine, characterized in that:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23076982A JPS59122468A (en) | 1982-12-28 | 1982-12-28 | Preparation of 2-methoxy-6-methylaminopyridine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23076982A JPS59122468A (en) | 1982-12-28 | 1982-12-28 | Preparation of 2-methoxy-6-methylaminopyridine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59122468A JPS59122468A (en) | 1984-07-14 |
| JPS632550B2 true JPS632550B2 (en) | 1988-01-19 |
Family
ID=16912971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23076982A Granted JPS59122468A (en) | 1982-12-28 | 1982-12-28 | Preparation of 2-methoxy-6-methylaminopyridine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59122468A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004069802A1 (en) * | 2003-02-06 | 2004-08-19 | Shionogi & Co., Ltd. | Process for producing 2-amino-3-substituted pyridine |
-
1982
- 1982-12-28 JP JP23076982A patent/JPS59122468A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59122468A (en) | 1984-07-14 |
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