Water → 2-Trifluoromethyl-4-(3-cyanophenyl)-4, 6,7,8-tetrahydro-5(1H)-quinolone

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Reaction Steps

A stirred solution of (-)-4-(3-cyanophenyl)-2-trifluoromethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid (3.93 g, 10.85 mmol) in N-methylpyrrolidin-2-one (24 mL) was placed in a preheated oil bath at 210° C. for 20 minutes. The cooled reaction mixture was then poured into water (200 mL) and extracted twice with ethyl ether. The combined ether extracts were washed twice with water, dried (MgSO4), filtered and the solvent removed to yield an off-white solid. Chromatography (eluent: methylene chloride/ether 9:1) and trituration with ethyl ether/hexane provided the title compound (3.42 g, 79%) as a white solid mp 187°-189° C. NMR: 1.88-1.91 (m, 2H, CH2), 2.21-2.25 (m, 2H, CH2), 2.53-2.64 (m, 2H, CH2), 4.68(d, 1H, J=5.3 Hz, CH), 5.61 (d, 1H, J=5.3 Hz, CH), 7.50-7.54 (m, 2H, Ar), 7.61-7.66 (m, 2H, Ar), 9.42 (s, 1H, NH); MS: m/z=319(M+1); [α]D23 =-606.8° (c=0.665, methanol). Analysis for C17H13F3N2O: Calculated C, 64.14; H, 4.12; N, 8.80; Found: C, 64.07; H, 4.24; N, 8.78.

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