Acetic Acid → 3-{[(Benzyloxy)carbonyl]amino}-7-bromoquinoline-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of ethyl 3-{[(benzyloxy)carbonyl]amino}-7-bromoquinoline-2-carboxylate (887.5 mg, 2.067 mmol) and K3PO4 (1494 mg, 7.038 mmol), 1,4-dioxane (10.0 mL) was added, followed by water (10.0 mL). The mixture was heated at 100° C. for 3 h. After cooling to room temperature, the reaction mixture was diluted with water (50 mL). AcOH (1313 mg, 21.86 mmol) was added to adjust the pH to 5. The mixture was extracted with EtOAc (3×50 mL). The combined organic layer was washed with brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by flash chromatography on silica gel (0-15% MeOH in DCM) to give the sub-title compound as a yellow solid (632.0 mg, 76%). LCMS calc. for C18H14BrN2O4(M+H)+: m/z=401.0. found 401.0.

Provenance & Evidence