Method for producing quinolin-4(1h)-one derivative

A method for producing a quinolone derivative represented by general formula (7):

• wherein R1, R2, R6, and X2 are as defined below,
• the method comprising using an aluminum halide represented by general formula (1):
• [Chemical Formula 1]
• AIZ3 (1)
• wherein Z represents a halogen atom,
• reacting a ketone represented by general formula (2):
• wherein
• R1 and R2 each independently represent:
• an optionally substituted linear or branched C1-4 alkyl group,
• an optionally substituted linear or branched C2-4 alkenyl group,
• an optionally substituted linear or branched C2-4 alkynyl group,
• an optionally substituted C3-8 cyclic aliphatic hydrocarbon group,
• an optionally substituted aromatic hydrocarbon group, or
• an optionally substituted heterocyclic group,
• alternatively, R1 and R2 are combined together to represent a group —(CH2)p— (in which p represents 2 to 6),
• wherein each of the substituents in the linear or branched C1-4 alkyl group, the linear or branched C2-4 alkenyl group and the linear or branched C2-4 alkynyl group is at least one group selected from the group consisting of a halogen atom, and a C1-4 alkoxy group optionally substituted with a halogen atom,
• the substituent in the C3-8 cyclic aliphatic hydrocarbon group is at least one group selected from the group consisting of a linear or branched C1-4 alkyl group, a halogen atom, and a C1-4 alkoxy group optionally substituted with a halogen atom,
• the substituent in the aromatic hydrocarbon group is at least one group selected from the group consisting of a halogen atom, a linear or branched C1-4 alkyl group optionally substituted with a halogen atom, a linear or branched C1-4 alkoxy group optionally substituted with a halogen atom, and a phenoxy group which is optionally substituted with a linear or branched C1-4 alkoxy group optionally substituted with a halogen atom, and
• the substituent in the heterocyclic group is at least one group selected from the group consisting of a halogen atom, a linear or branched C1-4 alkyl group optionally substituted with a halogen atom, and a linear or branched C1-4 alkoxy group optionally substituted with a halogen atom,
• with an anthranilic acid derivative represented by general formula (6):
• wherein
• R5 represents:
• an optionally substituted linear or branched C1-4 alkyl group, or
• an optionally substituted C3-8 cyclic aliphatic hydrocarbon group,
• R6 represents a hydrogen atom, a halogen atom, or —B—R7,
• wherein,
• B represents:
• an oxygen atom, a sulfur atom, N(R8), N(R8)—CO, or CO—N(R8),
• R7 and R8 each independently represent:
• a hydrogen atom,
• an optionally substituted linear or branched C1-4 alkyl group,
• an optionally substituted linear or branched C2-4 alkenyl group,
• an optionally substituted linear or branched C2-4 alkynyl group,
• an optionally substituted C3-8 cyclic aliphatic hydrocarbon group,
• an optionally substituted aromatic hydrocarbon group, or
• an optionally substituted heterocyclic group,
• wherein each of the substituents in the linear or branched C1-4 alkyl group, the linear or branched C2-4 alkenyl group, and the linear or branched C2-4 alkynyl group is at least one group selected from the group consisting of a halogen atom, and a C1-4 alkoxy group optionally substituted with a halogen atom,
• the substituent in the C3-8 cyclic aliphatic hydrocarbon group is at least one group selected from the group consisting of a linear or branched C1-4 alkyl group, a halogen atom, and a C1-4 alkoxy group optionally substituted with a halogen atom, and
• each of the substituents in the aromatic hydrocarbon group and the heterocyclic group is at least one group selected from the group consisting of:
• a halogen atom,
• a linear or branched C1-4 alkyl group optionally substituted with a halogen atom,
• a linear or branched C1-4 alkyl group which is optionally substituted with a C1-4 alkoxy group optionally substituted with a halogen atom,
• a linear or branched C2-4 alkenyl group optionally substituted with a halogen atom,
• a linear or branched C2-4 alkenyl group which is optionally substituted with a C1-4 alkoxy group optionally substituted with a halogen atom,
• a linear or branched C2-4 alkynyl group optionally substituted with a halogen atom,
• a linear or branched C2-4 alkynyl group which is optionally substituted with a C1-4 alkoxy group optionally substituted with a halogen atom,
• a linear or branched C1-4 alkoxy group optionally substituted with a halogen atom,
• a linear or branched C1-4 alkoxy group which is optionally substituted with a C1-4 alkoxy group optionally substituted with a halogen atom,
• a linear or branched C2-4 alkenyloxy group optionally substituted with a halogen atom,
• a linear or branched C2-4 alkenyloxy group which is optionally substituted with a C1-4 alkoxy group optionally substituted with a halogen atom,
• a linear or branched C2-4 alkynyloxy group optionally substituted with a halogen atom,
• a linear or branched C2-4 alkynyloxy group which is optionally substituted with a C1-4 alkoxy group optionally substituted with a halogen atom, and
• a phenoxy group which is optionally substituted with a linear or branched C1-4 alkoxy group optionally substituted with a halogen atom, and
• X2 represents:
• a hydrogen atom,
• a halogen atom,
• an optionally substituted linear or branched C1-4 alkyl group, or
• an optionally substituted linear or branched C1-4 alkoxy group,
• in which each of the substituents in the linear or branched C1-4 alkyl group, and the linear or branched C1-4 alkoxy group is at least one group selected from the group consisting of a halogen atom, and a C1-4 alkoxy group optionally substituted with a halogen atom;
• and removing the aluminum halide under basic conditions.