Sodium Hydroxide → 6-Chloro-4-(3-chloro-phenyl)-2-cyclopropyl-quinoline-3-carboxylic acid

Participants

Reaction Steps

To a white suspension of methyl 6-chloro-4-(3-chlorophenyl)-2-cyclopropylquinoline-3-carboxylate (45 mg, 0.12 mmol, 1 eq) in ethanol (2 ml) was added 1N NaOH (604 μl, 0.60 mmol, 5 eq) and the reaction mixture was refluxed overnight. The clear solution was then cooled to room temperature and concentrated in vacuo. The residue was diluted with water and the pH was adjusted to 3 with 1N HCl. The aqueous layer was extracted with ethyl acetate (×3) and the organic phases were combined and washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (1:1 ethyl acetate:heptane with 5% AcOH) to give 6-chloro-4-(3-chloro-phenyl)-2-cyclopropyl-quinoline-3-carboxylic acid (32 mg, 74%) as a white solid. MS (ESI): 358.1 (M+H)+.

Provenance & Evidence