Hydrochloric Acid → 2-(pyridin-3-yl)-4-(2-chloro-4-fluorophenyl)-4,6,7,8-tetrahydroquinazolin-5(1H)-one

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Reaction Steps

3-pyridinecarboxamidine hydrochloride (Schaefer F. C., Peters G. A., et al. J. Org. Chem.; 1961; 26(2); 412-418.) 2.164 mmol, 2-chloro-4-fluorobenzaldehyde 2.164 mmol, 1,3-cyclohexanedione 2.164 mmol and sodium acetate 3.2 mmol were reacted in 8 ml of anhydrous ethanol under reflexing for 18 hr, condensed, to which ethyl acetate, water and 1N HCl were added and then the layers were separated. The water layer was adjusted with concentrated NaOH solution until the pH to be basic, then ethyl acetate was added and extracted twice. The organic layers were combined, dried over anhydrous sodium sulfate and separated by column chromatography to obtain a yellow solid of 0.21 g (yield 27%); 1H-NMR (400 MHz, CDCl3) δ 2.13-2.17 (2H, m, CH2); 2.43-2.51 (2H, m, CH2); 2.63-2.83 (2H, m, CH2); 6.06 (1H, s, CH); 7.15-7.22 (2H, m, ArH); 7.34-7.38 (1H, m, ArH); 8.07-8.09 (1H, m, ArH); 8.70-8.71 (1H, m, ArH); 8.89 (1H, m, ArH). MS (HREI) 355.0887 (M+).

Provenance & Evidence