Perfluoroalkylated aniline compound and process for producing the same

An aniline derivative represented by the formula (I)

• 7
• wherein R1 and R2 may be the same or different and each denote a hydrogen atom, (C1-12)alkyl group, (C3-8)cycloalkyl group, hydroxy(C1-12)alkyl group, hydroxycarbonyl(C1-12)alkyl group, (C1-6)alkoxycarbonyl(C1-6)alkyl group, —COR8 (wherein R8 is a hydrogen atom, (C1-12)alkyl group, halo(C1-12)alkyl group, (C3-8)cycloalkyl group, phenyl group or phenyl group substituted with 1-5 groups, which may be the same or different, selected from the group consisting of cyano group, nitro group, hydroxyl group, halogen atom, (C1-6)alkyl group, halo(C1-6)alkyl group, (C1-6)alkoxy group, halo(C1-6)alkoxy group, carboxyl group and (C1-6)alkoxycarbonyl group) or COOR9 (wherein R9 is a (C1-6)alkyl group, halo(C1-6)alkyl group, phenyl group, phenyl group substituted with 1-5 groups, which may be the same or different, selected from the group consisting of cyano group, nitro group, hydroxyl group, halogen atom, (C1-6)alkyl group, halo(C1-6)alkyl group, (C1-6)alkoxy group, halo(C1-6)alkoxy group, carboxyl group and (C1-6)alkoxycarbonyl group, benzyl group or benzyl group substituted on the ring with 1-5 groups, which may be the same or different, selected from the group consisting of cyano group, nitro group, hydroxyl group, halogen atom, (C1-6)alkyl group, halo(C1-6)alkyl group, (C1-6)alkoxy group, halo(C1-6)alkoxy group, carboxyl group and (C1-6)alkoxy-carbonyl group);
• R3, R4, R5, R6 and R7 may be the same or different and each denote a hydrogen atom, halogen atom, hydroxyl group, nitro group, (C1-12)alkyl group, halo(C1-12)alkyl group, (C1-12)alkoxy group, halo(C1-12)alkoxy group, (C1-12)alkylthio group, halo(C1-12)alkylthio group, (C1-6)alkylthio(C1-6)alkyl group, hydroxy(C1-6)alkyl group, amino (C1-6)alkyl group, amino(C1-6)alkyl group substituted with one or two (C1-6)alkyl groups which may be the same or different, phenyl group, phenyl group substituted with 1-5 groups, which may be the same or different, selected from the group consisting of cyano group, nitro group, halogen atom, (C1-6)alkyl group, halo(C1-6)alkyl group, (C1-6)alkoxy group and halo(C1-6)alkoxy group, phenoxy group, phenoxy group substituted with 1-5 groups, which may be the same or different, selected from the group consisting of cyano group, nitro group, halogen atom, (C1-6)alkyl group, halo(C1-6)alkyl group, (C1-6)alkoxy group, and halo(C1-6)alkoxy group, benzyl group, benzyl group substituted on the ring with 1-5 groups, which may be the same or different, selected from the group consisting of cyano group, nitro group, halogen atom, (C1-6)alkyl group, halo(C1-6)alkyl group, (C1-6)alkoxy group and halo(C1-6)alkoxy group, —N(R10)R11 (wherein R10 and R11 maybe the same or different and are each a hydrogen atom, (C1-12)alkyl group, (C3-8)cycloalkyl group, phenyl group, phenyl group substituted with 1-5 groups, which may be the same or different, selected from the group consisting of cyano group, nitro group, hydroxyl group, halogen atom, (C1-6)alkyl group, halo(C1-6)alkyl group, (C1-6)alkoxy group, halo(C1-6)alkoxy group, carboxyl group and (C1-6)alkoxycarbonyl group, benzyl group, benzyl group substituted on the ring with 1-5 groups, which may be the same or different, selected from the group consisting of cyano group, nitro group, hydroxyl group, halogen atom, (C1-6)alkyl group, halo(C1-6)alkyl group, (C1-6)alkoxy group, halo(C1-6)alkoxy group, carboxyl group and (C1-6)alkoxycarbonyl group, —COR8, wherein R8 has the same meaning as defined above, or —COOR9, wherein R9 has the same meaning as defined above, further R10 and R11 may conjointly from a (C3-6)alkylene group), or (C2-27)perfluoroalkyl group;
• and further, R1 or R2 and R3 or R7 may conjointly form a (C2-4)alkylene group, and R3, R4, R5, R6 and R7 may form, with their two adjacent substituents joined together, a (C3-5)alkylene group or (C1-2)alkylenedioxy group, and at least one of the R3, R4, R5, R6 and R7 must denote, a (C2-27)perfluoroalkyl group;
• provided that
• (1) when R1, R2, R4 and R7 are each a hydrogen atom, R3 is a fluorine atom and R6 is a hydrogen atom, fluorine atom or chlorine atom, or when R1, R2, R3 and R6 are each a hydrogen atom, R7 is a fluorine atom and R4 is a hydrogen atom, fluorine atom or chlorine atom, then R5 must not be a pentafluoroethyl group or heptafluoro-n-propyl group,
• (2) when R1 and R2 are each a hydrogen atom, R3 is a methyl group and R4, R6 and R7 are simultaneously each a hydrogen atom, or when R1 and R2 are each a hydrogen atom, R7 is a methyl group and R3, R4 and R6 are simultaneously each a hydrogen atom, then R5 must not be a pentafluoroethyl group, heptafluoropropyl group, nonafluoro-n-butyl group or nonafluoro-sec-butyl group,
• (3) when R1 and R2 are each a hydrogen atom, R3 is a methyl group and R5, R6 and R7 are simultaneously each a hydrogen atom, or when R1 and R2 are each a hydrogen atom, R3, R5 and R6 are simultaneously each a hydrogen atom and R7 is a methyl group, then R4 must not be a pentafluoroethyl group,
• (4) when R1 and R2 are each a hydrogen atom, R3 is a methyl group and R4, R5 and R7 are simultaneously each a hydrogen atom, then R6 must not be a pentafluoroethyl group;
• or when R1 and R2 are each a hydrogen atom, R3, R5 and R6 are simultaneously each a hydrogen atom and R7 is a methyl group, then R4 must not be a pentafluoroethyl group,
• (5) when R1, R2, R4, R6 and R7 are simultanously each a hydrogen atom and R3 is a chlorine atom or when R1, R2, R3, R4 and R6 are simultaneously each a hydrogen atom and R7 is chlorine atom, then R5 must not be a pentafluoroethyl group, heptafluoropropyl group or nonafluoro-n-butyl group,
• (6) when R1, R2, R4, R6 and R7 are simultanously each a hydrogen atom and R3 is an ethyl group, n-butyl group, methoxy group or trifluoromethyl group or when R1, R2, R3, R4 and R5 are simultaneously each a hydrogen atom and R7 is an ethyl group, n-butyl group, methoxy group or trifluoromethyl group, then R5 must not be a pentafluoroethyl group,
• (7) when R1 and R2 are each a hydrogen atom and any four of the R3, R4, R5, R6 and R7 are simultanously each a hydrogen atom, then the remaining one of the R3, R4, R5, R6 and R7 must not be a heptafluoroisopropyl group,
• (8) when R1 and R2 are each a methyl group and R3, R4, R6 and R7 are simultanously each a hydrogen atom, then R5 must not be a heptafluoroisopropyl group,
• (9) when R1 and R2 are each a methyl group and R3, R5, R6 and R7 are simultanously each a hydrogen atom, then R4 must not be a heptafluoroisopropyl group,
• (10) when R1 and R2 are each a methyl group and R3, R4, R5 and R7 are simultaneously each a hydrogen atom, then R6 must not be a heptafluoroisopropyl group,
• (11) when R1, R2, R3 and R6 are simultaneously each a hydrogen atom, R4 is an amino group and one of the R5 and R 7is a hydrogen atom, or when R1, R2, R4 and R7 are simultaneously each a hydrogen atom, R6 is an amino group and one of the R3 and R5 is a hydrogen atom, then the other of the two must not be a heptafluoroisopropyl group,
• (12) when R1, R2, R4, R5 and R7 are simultanously each a hydrogen atom and R6 is methoxy group or iodine atom, then R3 must not be a heptafluoroisopropyl group, and
• (13) when R1, R2, R3, R5 and R6 are simultanously each a hydrogen atom and R4 is methoxy group or iodine atom, then R7 must not be a heptafluoroisopropyl group.