Methyl 4-iodobenzoate → 2-Methoxy-6-[4-methoxycarbonylphenyl]quinoline

Participants

Reaction Steps

t-Butyllithium (30 cm3 of a 2.0M solution in n-pentane) was added dropwise at -70° to a stirred solution of 6-bromo-2-methoxyquinoline (7.14 g) in tetrahydrofuran (THF) (50 cm3) under nitrogen. After 10 minutes a solution of anhydrous zinc chloride (4.09 g) in THF (30 cm3) was added and the solution was allowed to warm to room temperature. A mixture of methyl 4-iodobenzoate (7.8 g) and tetrakis(triphenylphosphine)palladium (0) (0.32 g) was added and the mixture was heated under reflux for 1 hour. Volatile material was removed in vacuo and the residue was partitioned between chloroform (150 cm3) and a solution of ethylenediaminetetraacetic acid disodium salt (22.4 g) in water (400 cm3). The aqueous phase was further extracted with chloroform (2×100 cm3), and the combined and dried (MgSO4) organic extracts were evaporated to give a solid which was recrystallised from acetone to afford the title compound, m.p. 158°-161°, (6.81 g).

Provenance & Evidence