Hydrochloric Acid → 1-(4-Fluorophenyl)-6-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Compound D (500 mg, 1.28 mmol, 1.00 eq), potassium hydroxide (216 mg, 3.84 mmol, 3.00 eq), tris(dibenzylideneacetone)dipalladium(0) (70.4 mg, 0.0769 mmol, 0.0600 eq) and 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (65.3 mg, 0.154 mmol, 0.120 eq) were suspended in a mixture of 1,4-dioxane (3.2 mL) and water (3.2 mL) in a microwave vial and heated in a microwave reactor at 150° C. for 15 minutes. The reaction was neutralized with 2N HCl and the mixture was diluted with ethyl acetate and washed with water. The organic phase was dried (MgSO4), filtered and concentrated in vacuo to afford 383 mg (99%) of the title compound as a brown solid that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.56 (s, 1H), 7.75-7.72 (m, 2H), 7.67 (d, J=2.7 Hz, 1H), 7.51 (t, J=8.7 Hz, 2H), 7.26 (d, J=9.1 Hz, 1H), 6.99 (d, J=9.2 Hz, 1H); ES-MS [M+1]+: 300.2.

Provenance & Evidence