Ethyl 2-oxocyclohexanecarboxylate → 2-(Trifluoromethyl)-5,6,7,8-tetrahydroquinazolin-4-ol

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Reaction Steps

To 10 mL of absolute ethanol under a nitrogen atmosphere was added 0.15 g of sodium metal. After all the sodium had reacted, 1.00 g of 2-carboethoxycyclohexanone was added followed by 0.78 g of 85% trifluoroacetamidine. The reaction was refluxed gently overnight. The reaction was cooled to room temperature and all solvents were removed by evaporation. The pH of the residue was adjusted to 6 with dilute hydrochloric acid and refluxed briefly and allowed to cool. The resulting solid was collected. (0.73 g, 57%): 1H NMR (DMSO-d6, 300 MHz) δ 13.0 (s, 1H), 2.78 (m, 2H), 2.45 (m, 2H), 1.78 (m, 4H).

Provenance & Evidence