3,4-DIHYDROQUINAZOLIN-2(1H)-ONE synthesis
- Product Name:3,4-DIHYDROQUINAZOLIN-2(1H)-ONE
- CAS Number:66655-67-2
- Molecular formula:C8H8N2O
- Molecular Weight:148.16
32315-10-9
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Yield: 99%
Reaction Conditions:
in tetrahydrofuranInert atmosphere;
Steps:
3,4-Dihydroquinazolin-2(1H)-one (10b)
Triphosgene (3.31 g, 12.3 mmol) was added toa solution of 2-(aminomethyl)aniline (1.50 g, 12.3 mmol) in 30 ml THF under a nitrogenatmosphere. After precipitation of a colorless solid, stirring was continued for 30 minbefore water was added. The solution was extracted several times with ethyl acetate. Thecombined organic layers were washed with brine and dried over anhydrous MgSO4 toafford 10b (1.80 g, 12.2 mmol, 99 %) as colorless solid. 1H-NMR (500 MHz, DMSO-d6):δ = 4.30 (s, 2H), 6.75-6.77 (m, 2H), 6.84 (ddd, 3J = 3J = 7.4 Hz, 4J = 1.9 Hz, 1H), 7.06 (d,3J = 7.3 Hz, 1H), 7.09 (dd, 3J = 3J = 7.7 Hz, 1H), 8.98 (s, 1H). 13C-NMR (125 MHz,DMSO-d6): δ = 42.4, 113.4, 118.0, 120.8, 125.5, 127.4, 138.0, 154.5.
References:
Grombein, Cornelia M.;Hu, Qingzhong;Rau, Sabrina;Zimmer, Christina;Hartmann, Rolf W. [European Journal of Medicinal Chemistry,2015,vol. 90,p. 788 - 796] Location in patent:supporting information
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