Method of producing aromatic amide derivative

A method of producing an aromatic amide derivative of the following Formula (I), comprising the following process a and process b:

• in Formula (I), R1 represents a halogen atom;
• a C1-C4 haloalkyl group;
• or a C1-C4 haloalkyl group substituted by 1 to 8 substituents, which may be the same or different, selected from the group consisting of a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylamino group, a di-C1-C4 alkylamino group, a cyano group, and a nitro group;
• each of X1 and X2 independently represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4 alkylamino group, a cyano group, a nitro group, a C1-C4 alkylcarbonyl group, or a C1-C4 haloalkylcarbonyl group;
• each of R2 and R3 independently represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4 alkylamino group, a cyano group, or a nitro group;
• R4 represents:
• a hydrogen atom;
• a C1-C4 alkyl group;
• a C1-C4 haloalkyl group;
• a C1-C4 alkylcarbonyl group;
• a C1-C4 haloalkylcarbonyl group;
• a C1-C4 alkoxycarbonyl group;
• a C1-C4 haloalkoxycarbonyl group;
• a C1-C4 alkylsulfonyl group;
• a C1-C4 haloalkylsulfonyl group;
• or
• a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkoxycarbonyl group, a C1-C4 haloalkoxycarbonyl group, a C1-C4 alkylsulfonyl group, or a C1-C4 haloalkylsulfonyl group, substituted by 1 to 9 substituents, which may be the same or different, selected from the group consisting of a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4 alkylamino group, a C1-C4 alkylcarbonyl group, a C1-C4 alkoxycarbonyl group, a di-C1-C4 alkylaminocarbonyl group, a cyano group, and a nitro group;
• and
• Q represents:
• a C1-C4 alkyl group;
• a C1-C4 haloalkyl group;
• a C1-C4 alkylaminocarbonyl group;
• a C1-C4 haloalkylaminocarbonyl group;
• a di-C1-C4 alkylaminocarbonyl group;
• a di-C1-C4 haloalkylaminocarbonyl group;
• a phenyl group;
• a heterocyclic group;
• a C1-C4 alkyl group or a C1-C4 haloalkyl group, substituted by 1 to 9 substituents, which may be the same or different, selected from the group consisting of a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylamino group, a di-C1-C4 alkylamino group, a cyano group, and a nitro group;
• a phenyl group substituted by 1 to 5 substituents, which may be the same or different, selected from the group consisting of a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylamino group, a di-C1-C4 alkylamino group, a cyano group, and a nitro group;
• or
• a heterocyclic group substituted by 1 to 4 substituents, which may be the same or different, selected from the group consisting of a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylamino group, a di-C1-C4 alkylamino group, a cyano group, and a nitro group;
• wherein the heterocyclic group is a pyridyl group, a pyridyl-N-oxide group, a pyrimidyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group, or a tetrazolyl group;
• and
• wherein the process a comprises reacting an aniline derivative of the following Formula (II) with a carboxylic acid derivative of the following Formula (III), in the presence of a base, to thereby obtain an imide compound of the following Formula (IV):
• in Formula (II), R1, X1, and X2 are the same as R1, X1, and X2 in Formula (I),
• in Formula (III), X3 represents a halogen atom or a C1-C4 alkoxy group, and R2, R3, R4, and Q are the same as R2, R3, R4, and Q in Formula (I),
• in Formula (IV), R1, X1, X2, R2, R3, R4, and Q are the same as R1, X1, X2, R2, R3, R4, and Q in Formula (I), and two of R2, R3, R4 and Q may be the same or different at each occurrence, respectively;
• and
• the process b comprises hydrolyzing the imide compound of Formula (IV), to thereby obtain the aromatic amide derivative of Formula (I).