Potassium Acetate → 5-amino-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one

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Reaction Steps

A mixture of 5-amino-7-chloro-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one (8.0 g, 28 mmol), KOAc (5.6 g, 57 mmol) and 10% Pd—C (4.0 g) in 200 mL ethanol was stirred under an atmosphere of hydrogen for 2 h. The mixture was filtered through Celite and concentrated under reduced pressure. The resultant solid was dissolved in EtOAc (250 mL) and washed sequentially with saturated NaHCO3 (200 mL) and brine (200 mL), dried over MgSO4, filtered and concentrated to afford 7.0 g (100%) of 5-amino-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one, a foamy tan solid. 1H NMR (400 MHz, acetone-d6) δ 9.16 (broad s, 1H), 6.99 (t, 1H, J=8.0), 6.44 (broad s, 1H), 6.39 (d, 1H, J=7.9), 6.26 (d, 1H, J=7.9), 5.44 (broad s, 2H), 3.09 (d, AB, J=17.0), 2.93 (d, AB, J=17.0).

Provenance & Evidence