7-Oxo-7-phenylheptanoic acid → 5-(6-Bromo-2-phenylquinolin-3-yl)pentanoic acid

Participants

Reaction Conditions

Reaction Steps

7-Oxo-7-phenylheptanoic acid (5.00 g, 22.7 mmol) and 2-amino-5-bromobenzaldehyde (5.45 g, 27.2 mmol) were dissolved in a solution of methanol (100 mL) and 2 M NaOH (30 mL). The reaction mixture was heated to 110° C. in an oil bath and refluxed overnight. The reaction was concentrated, acidified with 10% aq. HCl to pH 1 and diluted with DCM. The biphasic solution was separated and the aqueous layer was extracted with DCM (3×). The combined organic phase was dried over anhydrous sodium sulfate and concentrated to provide 5-(6-bromo-2-phenylquinolin-3-yl)pentanoic acid (1A, 8.97 g, LCMS (M+H)=384).

Provenance & Evidence