3-Nitrobenzaldehyde → 3-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

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Reaction Steps

A stirred mixture of ethyl 4,4,4-trifluoroacetoacetate (6.00 mL), 1,3-cylohexanedione (4.65 g), 3-nitrobenzaldehyde (6.31 g), and ammonium acetate (6.57 g) in ethanol (350 mL) was heated at reflux for 4.5 hours. After removal of solvent the orange residue was treated diethyl ether, and the resulting precipitate was collected by filtration. The solid was triturated with hot diethyl ether, collected, and purified by chromatography (ethyl acetate) to yield 3-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone (8.47 g) as a white solid. NMR: 0.85 (t,3, J=7.1, CH3), 1.86 (m,2, CH2), 2.07 (m,2, CH2), 2.27-2.44 (m,1, CH2), 2.57-2.72 (m,1, CH2), 2.75 (d,1, J=11.9, CH), 3.83 (m,2, CH2), 4.07 (d,1, J=11.4, CH), 7.30 (s,1, OH), 7.50 (m,1, Ar), 7.57 (m,1, Ar), 7.87 (m,1, Ar), 8.01 (m,1, Ar), 8.16 (s,1, NH); MS: m/z=428(M).

Provenance & Evidence