Hydrochloric Acid → 2-(pyridin-3-yl)-4-(2-chloro-4-fluorophenyl)-7,7-dimethyl-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, 5,5-dimethyl-1,3-cyclohexanedione 2.164 mmol and sodium acetate 3.2 mmol were reacted in 8 ml of anhydrous ethanol under refluxing for 18 hr, condensed, and ethyl acetate and water and 1N HCl were added to separate the layers. 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 0.22 g (yield 26%); mp 186-187° C. 1H-NMR (400 MHz, CDCl3) δ 1.15 (3H, s, CH3); 1.16 (3H, s, CH3); 2.31 (2H, s, CH2); 2.53-2.69 (2H, m, CH2); 6.07 (1H, s, CH); 6.94-6.96 (1H, m, ArH); 7.14-7.17 (1H, m, ArH); 7.23-7.26 (1H, m, ArH); 7.34-7.38 (1H, m, ArH) 8.07-8.09 (1H, m, ArH); 8.69-8.71 (1H, m, ArH); 8.89 (1H, m, ArH). MS (EI) 383.1 (M+).

Provenance & Evidence