Ishihara Sangyo Kaisha, Ltd.

Fumihiro Fukui

Hisayoshi Jonishi

Fumio Kanamori

Shigehisa Kanbayashi

Tokiya Kimura

Tomohiro Okamoto

Hideaki Konishi

Norio Adachi

Akihiko Isogai

Tatsuya Jukurogi

Noriyuki Horiuchi

Tooru Wakabayashi

Akimasa Takenaka

To provide an industrial method for producing a substituted benzoic acid compound useful as an intermediate of pharmaceutical and agricultural chemicals with high purity and high yield. A compound represented by the formula (II): (wherein Q is a 5- or 6-membered saturated heterocyclic group (the heterocyclic group may be substituted by alkyl) containing one or two of at least one type of hetero atom selected from the group consisting of an oxygen atom and a sulfur atom, or dialkoxymethyl, T is trifluoromethyl, nitro, cyano, &#x2014;SOA, &#x2014;SOA, &#x2014;PO(OA)(OA), &#x2014;COA, &#x2014;COAor &#x2014;CONAA, each of Aand Awhich are independent of each other, is a hydrogen atom, alkyl or haloalkyl, X is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, di(haloalkyl)aminosulfonyl, nitro or cyano, Y is a chlorine atom, a bromine atom or an iodine atom, and n is an integer of from 1 to 6), carbon monoxide and a compound represented by the formula R&#x2014;OH (wherein R is alkyl) are reacted, followed by hydrolysis to obtain a compound represented by the formula (I): wherein Q, T, X and n are as defined above.

Method for producing a substituted benzoic acid compound

The present invention provides processes for producing 2-chloro-3-trifluoromethylpyridine which is useful as an intermediate for medicines and agrochemicals, at a high production rate in a high yield. Specifically, the present invention relates to a process for producing 2-chloro-3-trifluoromethylpyridine or a salt thereof comprising allowing 3-trifluoromethylpyridine N-oxide to react with a chlorinating agent; and also relates to a process for producing 2-chloro-3-trifluoromethylpyridine or a salt thereof comprising oxidizing 3-trifluoromethylpyridine to produce 3-trifluoromethylpyridine N-oxide and subsequently allowing the obtained 3-trifluoromethylpyridine N-oxide to react with a chlorinating agent.

Processes for producing 2-chloro-3-trifluoromethylpyridine

A process for producing 1-substituted-2-cyanoimidazole compounds is described, which comprises (1) undergoing a reaction of a compound represented by formula (IV), hydroxylamine or a mineral acid salt thereof, and glyoxal or glyoxime to produce a compound represented by formula (III), (2) undergoing a reaction of the compound represented by formula (III) with thionyl chloride or thionyl bromide in the presence of N,N-dialkylamide to produce a reaction mixture, and then reacting the produced reaction mixture with sulfur chloride to produce a 2-cyanoimidazole compound represented by formula (II), and (3) undergoing a sulfamoylation reaction and an isomerization reaction of the 2-cyanoimidazole compound represented by formula (II) and a compound represented by formula (V) in the presence of at least one base selected from carbonates of alkali metals and bicarbonates of alkali metals and a polar solvent to produce a 1-substituted-2-cyanoimidazole compound represented by formula (I-b). The formulae and substituents formulae are specifically defined in the specification. ##STR1##

Processes for producing 1-substituted-2-cyanoimidazole compounds

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Shiga, Japan

Fumihiro Fukui