Patent ID: 8367833

Claim:
A process for producing a quinoline derivative, the process comprising: (i) a cyclization reaction step (C) of reacting an anthranilic acid derivative represented by general formula (1): wherein R 1 , R 2 , and R 3 each independently represent a hydrogen atom, a halogen atom, C 1-4 alkyl optionally substituted by a halogen atom(s), or C 1-4 alkoxy optionally substituted by a halogen atom(s), provided that R 1 , R 2 , and R 3 do not simultaneously represent a hydrogen atom, R 4 represents a hydrogen atom or a protecting group of carboxylic acid, and R 5 , R 6 , R 7 , R 8 , and R 9 each independently represent a hydrogen atom, a halogen atom, C 1-8 alkyl optionally substituted by a halogen atom(s), C 1-8 alkoxy optionally substituted by a halogen atom(s), C 1-8 alkylthio optionally substituted by a halogen atom(s), C 2-4 alkenyloxy optionally substituted by a halogen atom(s), C 2-4 alkenylthio optionally substituted by a halogen atom(s), or C 2-4 alkynyloxy optionally substituted by a halogen atom(s), or any two adjacent substituents of R 5 , R 6 , R 7 , R 8 , and R 9 together represent —O—(CH 2 ) n —O— wherein n is 1 or 2, optionally substituted by one or more halogen atoms, with a ketone represented by general formula (2): wherein R 10 and R 11 each independently represent a hydrogen atom or C 1-4 alkyl optionally substituted by a halogen atom(s), or R 10 and R 11 together represent —(CH 2 ) m — wherein m is 3 or 4, provided that R 10 and R 11 do not simultaneously represent a hydrogen atom, in the presence of an acid to obtain a quinolone derivative of general formula (3): wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are as defined above; and (ii) a condensation reaction step (D) of reacting the quinolone derivative of general formula (3) with a halogen compound represented by general formula (4): wherein R 12 represents C 1-8 alkyl optionally substituted by a halogen atom(s), C 3-6 cyclic alkyl optionally substituted by a halogen atom(s), C 2-4 alkenyl optionally substituted by a halogen atom(s), OR 13 wherein R 13 represents C 1-8 alkyl optionally substituted by a halogen atom(s); C 3-6 cyclic alkyl optionally substituted by a halogen atom(s); or C 2-4 alkenyl optionally substituted by a halogen atom(s), or SR 14 wherein R 14 represents C 1-8 alkyl optionally substituted by a halogen atom(s); C 3-6 cyclic alkyl optionally substituted by a halogen atom(s); or C 2-4 alkenyl optionally substituted by a halogen atom(s), and Y represents any one of fluorine, chlorine, bromine, and iodine, or an acid anhydride represented by general formula (5): wherein R 12 is as defined above, to obtain a quinoline derivative represented by general formula (6): wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 are as defined above.