Process for the preparation of substituted 3-aminobenzonitriles

Details Process for the preparation of substituted 3-aminobenzonitriles Process for the preparation of substituted 3-aminobenzonitriles

C - Chemistry, Metallurgy

07

C

C07C 323/33 (2006.01) C07C 319/14 (2006.01) C07C 319/20 (2006.01) C07C 323/09 (2006.01) C07C 323/63 (2006.01) C07C 327/20 (2006.01) C07D 285/14 (2006.01) C07C 323/25 (2006.01) C07C 323/62 (2006.01)

Patent

CA 2201471

The invention relates to a process for the preparation of substituted 3- aminobenzonitriles of formula (I) in which: R is hydrogen or C1-C12alkyl, C3- C8cycloalkyl, COR1, C1-C8alkoxyalkyl, C1-C6hydroxyalkyl, C1-C8aminoalkyl, C1- C8alkyl-NH(C1-C4alkyl), C1-C8alkyl-N(C1-C4alkyl)2 or substituted or unsubstituted benzyl; and R1 is C1-C8alkyl, C3-C8cycloalkyl or phenyl; and which comprises reacting a substituted 3-aminochlorobenzene of formula (II) with a cyano-donating reagent. Compounds of formula (I) are important intermediates in the preparation of benzothiadiazole-7-carboxylic acid, which is obtained by diazotizing and hydrolysing the compounds of formula (I) in any desired sequence.

L'invention se rapporte à un procédé de préparation de 3-aminobenzonitriles substitués de la formule (I) dans laquelle R représente hydrogène ou alkyle C¿1?-C¿12?, cycloalkyle C¿3?-C¿8?, COR¿1?, alcoxyalkyle C¿1?-C¿8?, hydroxyalkyle C¿1?-C¿6?, aminoalkyle C¿1?-C¿8?, alkyle C¿1?-C¿8?-NH(alkyle C¿1?-C¿4?), alkyle C¿1?-C¿8?-N(alkyle C¿1?-C¿4?)¿2? ou benzyle substitué ou non substitué; et R¿1? représente alkyle C¿1?-C¿8?, cycloalkyle C¿3?-C¿8? ou phényle. Ce procédé consiste à faire réagir un 3-aminochlorobenzène substitué de la formule (II) avec un réactif donneur de cyano. Les composés de la formule (I) sont des intermédiaires importants dans la préparation de l'acide benzothiadiazole-7-carboxylique qui est obtenu par diazotation et hydrolyse des composés de la formule (I) dans n'importe quelle séquence désirée.

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