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1. 发明授权

US5696301A Process for preparing protocatechualdehyde 失效
标题翻译：原儿茶醛的制备方法
公开(公告)号：US5696301A
公开(公告)日：1997-12-09
申请号：US787583
申请日：1997-01-22
申请人： Katsumasa Harada , Masashi Shirai , Toshio Furuya , Nobuyuki Kuroda
发明人： Katsumasa Harada , Masashi Shirai , Toshio Furuya , Nobuyuki Kuroda
IPC分类号： C07C45/43 , C07D317/46 , C07C34/10 , C07D307/00 , C07D317/44
CPC分类号： C07D317/46 , C07C45/43
摘要： Protocatechualdehyde is prepared by the steps of reacting piperonyl dichloride with molecular chlorine in the presence of phosphorus trichloride, phosphorus pentachloride or sulfuryl chloride to prepare dichloropiperonylidene dichloride and hydrolyzing the dichloropiperonylidene dichloride. The piperonyl dichloride can be prepared by the reaction of piperonal with thionyl chloride in the presence of dimethylformamide.
摘要翻译：通过在三氯化磷，五氯化磷或磺酰氯存在下使胡椒基二氯与分子氯反应的步骤制备原儿茶醛，制备二氯哌啶子基二氯化物并水解二氯磷酰二氯。胡椒基二氯化物可以通过胡椒醛与亚硫酰氯在二甲基甲酰胺存在下反应来制备。

2. 发明授权

US06686482B2 Process for preparing piperonal 失效
标题翻译：胡椒醛的制备方法
公开(公告)号：US06686482B2
公开(公告)日：2004-02-03
申请号：US10182485
申请日：2002-07-30
申请人： Katsumasa Harada , Masashi Shirai , Koji Shiba , Toshio Furuya
发明人： Katsumasa Harada , Masashi Shirai , Koji Shiba , Toshio Furuya
IPC分类号： C07D31754
CPC分类号： C07D317/54
摘要： The present invention is to provide a process for producing piperonal which comprises continuous three steps of: (A) an addition reaction step wherein 1,2-methylenedioxybenzene and glyoxylic acid are reacted to form 3,4-methylenedioxymandelic acid in the presence of a strong acid, (B) an extraction step wherein an organic solvent is then added to a reaction mixture and the mixture is neutralized with a base to extract 3,4-methylenedioxymandelic acid in an organic solvent layer, and separating the organic solvent layer and an aqueous layer, and (C) an oxidation reaction step wherein the aqueous layer is removed and the organic solvent layer is concentrated, and then, nitric acid is added to a concentrate, and the 3,4-methylenedioxymandelic acid and nitric acid are reacted to form piperonal.
摘要翻译：本发明提供一种生产胡椒醛的方法，其包括连续三个步骤：（A）加成反应步骤，其中1,2-亚甲二氧基苯和乙醛酸在强的存在下反应形成3,4-亚甲二氧基扁桃酸酸，（B）提取步骤，其中将有机溶剂加入到反应混合物中，并将混合物用碱中和以在有机溶剂层中提取3,4-亚甲二氧基扁桃酸，并将有机溶剂层和水性层，和（C）氧化反应步骤，其中除去水层并浓缩有机溶剂层，然后向浓缩物中加入硝酸，并使3,4-亚甲二氧基扁桃酸和硝酸反应形成胡椒醛

3. 发明授权

US06603024B1 Process for the preparation of 3,4-methylenedioxymandelic acid 失效
标题翻译：制备3,4-亚甲二氧基扁桃酸的方法
公开(公告)号：US06603024B1
公开(公告)日：2003-08-05
申请号：US10110263
申请日：2002-04-02
申请人： Katsumasa Harada , Masashi Shirai , Koji Shiba
发明人： Katsumasa Harada , Masashi Shirai , Koji Shiba
IPC分类号： C07D32302
CPC分类号： C07D317/60
摘要： A process for preparing 3,4-methylenedioxymandelic acid by reacting 1,2-methylenedioxybenzene with glyoxylic acid in the presence of a strong acid and of at least one substance selected from the group consisting of an aprotic organic solvent and 100 to 1200 ml of an organic acid per kg of 1,2-methylenedioxybenzene.
摘要翻译：一种通过1,2-亚甲二氧基苯与乙醛酸在强酸和至少一种选自非质子有机溶剂和100至1200ml 有机酸/ kg 1,2-亚甲二氧基苯。

4. 发明授权

US07342040B2 5-fluorooxindole-3-carboxylic acid ester 失效
标题翻译： 5-氟羟吲哚-3-羧酸酯
公开(公告)号：US07342040B2
公开(公告)日：2008-03-11
申请号：US11093603
申请日：2005-03-30
申请人： Katsumasa Harada , Shigeyoshi Nishino , Kenji Hirotsu , Shuji Yokoyama , Takeshi Takahashi , Hiroyuki Oda
发明人： Katsumasa Harada , Shigeyoshi Nishino , Kenji Hirotsu , Shuji Yokoyama , Takeshi Takahashi , Hiroyuki Oda
IPC分类号： A61K31/404 , C07D209/04
CPC分类号： C07D209/34 , C07C201/12 , C07C205/56 , C07C255/41 , C07D209/32
摘要： A 5-fluorooxindole-3-carboxylic acid ester represented by a formula (2): wherein R1 is a group selected from the group consisting of an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted cycloalkyl group having 3 to 7 carbon atoms, an aralkyl group having 7 to 10 carbon atoms or an aryl group having 6 to 14 carbon atoms.
摘要翻译：由式（2）表示的5-氟羟吲哚-3-羧酸酯：其中R 1是选自未取代或取代的碳原子数1〜10的烷基，具有3至7个碳原子的未取代或取代的环烷基，具有7至10个碳原子的芳烷基或具有6至14个碳原子的芳基。

5. 发明授权

US06900335B2 Process for producing 5-fluorooxindole and for producing intermediates therefor 失效
标题翻译：制备5-氟羟吲哚的方法及其制备中间体
公开(公告)号：US06900335B2
公开(公告)日：2005-05-31
申请号：US10333316
申请日：2001-07-19
申请人： Katsumasa Harada , Shigeyoshi Nishino , Kenji Hirotsu , Shuji Yokoyama , Takeshi Takahashi , Hiroyuki Oda
发明人： Katsumasa Harada , Shigeyoshi Nishino , Kenji Hirotsu , Shuji Yokoyama , Takeshi Takahashi , Hiroyuki Oda
IPC分类号： C07C205/56 , C07C255/41 , C07D209/32 , C07D209/34
CPC分类号： C07D209/34 , C07C201/12 , C07C205/56 , C07C255/41 , C07D209/32
摘要： The present invention discloses a process for preparing 5-fluorooxindole represented by the formula (3): which comprises (A) a first step of cyclizing 2-(5-fluoro-2-nitrophenyl)malonic acid diester represented by the formula (1): wherein R1 and R2 may be the same or different from each other and each represents a group which does not participate in the reaction, under reductive conditions to form 5-fluorooxindole-3-carboxylic acid ester represented by the formula (2): wherein R1 has he same meaning as defined above, and (B) then, a second step of decarboxylating the 5-fluorooxindole-3-carboxylic acid ester, and a process for preparing its synthetic intermediates.
摘要翻译：本发明公开了一种制备式（3）表示的5-氟羟吲哚的方法：其包括（A）使由式（1）表示的2-（5-氟-2-硝基苯基）丙二酸二酯环化的第一步骤，：其中R 1和R 2彼此可以相同或不同，并且各自代表不参与反应的基团，在还原条件下形成5- 由式（2）表示的氟氧吲哚-3-羧酸酯：其中R 1具有与上述相同的含义，（B）然后，将5-氟羟吲哚-3 - 羧酸酯及其合成中间体的制备方法。

6. 发明授权

US06841681B2 Process for producing quinoline carboxyaldehyde derivative and intermediate thereof 失效
标题翻译：制备喹啉羧醛衍生物及其中间体的方法
公开(公告)号：US06841681B2
公开(公告)日：2005-01-11
申请号：US10468062
申请日：2002-02-14
申请人： Katsumasa Harada , Shigeyoshi Nishino , Kenji Hirotsu , Hidetaka Shima , Naoko Okada , Takashi Harada , Akira Nakamura , Hiroyuki Oda
发明人： Katsumasa Harada , Shigeyoshi Nishino , Kenji Hirotsu , Hidetaka Shima , Naoko Okada , Takashi Harada , Akira Nakamura , Hiroyuki Oda
IPC分类号： C07D215/14 , C07D215/54 , C07C225/22 , C07C255/17 , C07D215/12
CPC分类号： C07D215/14
摘要： 2-Cyclopropyl-4-(4′-fluorophenyl)quinoline-3-carboxyaldehyde useful as a material for pharmaceutical products, can be obtained by reacting 3-cyclopropyl-3-oxopropanenitrile with 2-amino-4′-fluorobenzophenone to obtain 2-cyclopropyl-4-(4′-fluorophenyl)quinoline-3-carbonitrile, and reducing it.
摘要翻译：可用作药物物质的2-环丙基-4-（4'-氟苯基）喹啉-3-甲醛可以通过3-环丙基-3-氧代丙腈与2-氨基-4'-氟二苯甲酮反应得到2- 环丙基-4-（4'-氟苯基）喹啉-3-腈，并还原。

7. 发明授权

US5178663A 3-alkoxyalkanoic acid derivative, process for preparing the same and herbicide using the same 失效
标题翻译： 3-烷氧基甘氨酸衍生物，其制备方法和使用其的除草剂
公开(公告)号：US5178663A
公开(公告)日：1993-01-12
申请号：US779238
申请日：1991-10-18
申请人： Katsumasa Harada , Takaaki Abe , Yuji Akiyoshi , Hiroshi Shiraishi , Kaoru Yamamoto
发明人： Katsumasa Harada , Takaaki Abe , Yuji Akiyoshi , Hiroshi Shiraishi , Kaoru Yamamoto
IPC分类号： A01N43/54 , C07D239/34 , C07D239/38 , C07D239/52 , C07D239/60
CPC分类号： C07D239/60 , A01N43/54 , C07D239/34 , C07D239/38 , C07D239/52
摘要： Disclosed is a 3-alkoxyalkanoic acid compound represented by the following formula (I): ##STR1## wherein R.sup.1 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, a halo-lower alkyl group or a cyano-lower alkyl group; R.sup.2 represents hydrogen atom or a lower alkyl group; R.sup.3 represents a lower alkyl group or a cycloalkyl group; or R.sup.2 and R.sup.3 are mutually bonded to represent a cycloalkyl group; R.sup.4 represents hydrogen atom, a lower alkyl group or a lower alkynyl group; R.sup.5 represents a lower alkoxy group, a lower alkyl group, a halogen atom or a halo-lower alkyl group; R.sup.6 represents a lower alkoxy group or a lower alkyl group; andX represents oxygen atom or sulfur atom,or an alkali addition salt thereof, processes for preparing the same and herbicides containing the same as an active ingredient(s).

8. 发明授权

US4376080A Process for preparing malononitrile 失效
标题翻译：丙二腈的制备方法
公开(公告)号：US4376080A
公开(公告)日：1983-03-08
申请号：US324424
申请日：1981-11-24
申请人： Toshikazu Hamamoto , Katsumasa Harada
发明人： Toshikazu Hamamoto , Katsumasa Harada
IPC分类号： C07C120/00 , C07C121/22
CPC分类号： C07C255/00
摘要： Disclosed is a process for preparing malononitrile which comprises reacting diazoacetonitrile with hydrogen cyanide in the presence of a copper compound in a solvent. The diazoacetonitrile may be formed in a reaction mixture by reacting aminoacetonitrile with nitrous acid in a solvent, which is then subjected to the further reaction as such without isolating it from the reaction mixture.
摘要翻译：公开了一种制备丙二腈的方法，其包括在铜化合物存在下在溶剂中使重氮乙腈与氰化氢反应。重氮乙腈可以通过使氨基乙腈与亚硝酸在溶剂中反应而在反应混合物中形成，然后将其进一步反应，而不从反应混合物中分离。

9. 发明授权

US06541636B2 Process for preparing quinolylacrylonitrile and intermediates therefor 有权
标题翻译：制备喹啉基丙腈的方法及其中间体
公开(公告)号：US06541636B2
公开(公告)日：2003-04-01
申请号：US10181973
申请日：2002-07-24
申请人： Katsumasa Harada , Shigeyoshi Nishino , Naoko Okada , Hidetaka Shima , Takashi Harada
发明人： Katsumasa Harada , Shigeyoshi Nishino , Naoko Okada , Hidetaka Shima , Takashi Harada
IPC分类号： C07D21504
CPC分类号： C07D215/12
摘要： 3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrile is prepared by reacting 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde with acetonitrile in the presence of a base and then adding a dehydrating to the reaction mixture to conduct dehydration. Under ordinary conditions, novel 3-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxypropionitrile is formed as an intermediate in the above reaction. Incidentally, when the above reaction is conducted in an organic solvent, 3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-prop-2-enenitrile is directly formed.
摘要翻译： 3- [2-环丙基-4-（4-氟苯基）-3-喹啉基]丙-2-烯腈是通过2-环丙基-4-（4-氟苯基）喹啉-3-甲醛与乙腈在然后向反应混合物中加入脱水剂进行脱水。在常规条件下，在上述反应中形成新的3- [2-环丙基-4-（4-氟 - 苯基） - 喹啉-3-基] -3-羟基丙腈作为中间体。顺便提及，当上述反应在有机溶剂中进行时，直接形成3- [2-环丙基-4-（4-氟苯基）-3-喹啉基] - 丙-2-烯腈。

10. 发明授权

US06169209A Preparation of organic phosphonium chloride 有权
标题翻译：有机氯化鏻的制备
公开(公告)号：US06169209A
公开(公告)日：2001-01-02
申请号：US09200370
申请日：1998-11-23
申请人： Katsumasa Harada , Ryoji Sugise , Koichi Kashiwagi , Sadao Niida
发明人： Katsumasa Harada , Ryoji Sugise , Koichi Kashiwagi , Sadao Niida
IPC分类号： C07F954
CPC分类号： C07F9/54
摘要： An improved process for preparing an organic phosphonium chloride is performed by bringing an organic phosphonium bromide into contact with a chloride ion in a heterogeneous mixture solution of water and an organic solvent.
摘要翻译：通过使有机溴化鏻与水和有机溶剂的非均相混合溶液中的氯离子接触来进行制备有机氯化鏻的改进方法。

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