Methanol → HCID 59756874, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloro-6,7-dimethoxyquinoline (3 g, 13.45 mmol), palladium acetate (605 mg, 2.69 mmol) and 1,3-bis(diphenylphosphino)propane (1.39 g, 3.36 mmol) were added to a pressure tube then dissolved in N,N-dimethylformamide (25 mL). Carbon monoxide gas was bubbled through the mixture for 10-15 minutes. The reaction mixture was heated at 85° C. overnight. Additional palladium acetate (303 mg, 1.35 mmol), 1,3-bis(diphenylphosphino)propane (277 mg, 0.671 mmol) and methanol (2 mL) were added to the reaction mixture then carbon monoxide was bubbled through the solution for 10 minutes. The reaction mixture was then heated at 85° C. overnight again. The mixture was concentrated under vacuum. The crude material was purified twice by silica gel chromatography (1% methanol/dichloromethane then 50%-67% ethyl acetate/hexane) to afford methyl 6,7-dimethoxyquinoline-4-carboxylate (2.07 g) as a light yellow solid. MS (ESI, pos. ion) m/z: 248.0 (M+1).

Provenance & Evidence