反应详情

温度

90 °C

A mixture of 2,4-dichloro-8-phenyl-5,6,7,8-tetrahydroquinazoline (51.9 mg, 0.186 mmol), ammonium chloride (13.0 mg, 0.243 mmol) and zinc (130 mg, 1.988 mmol) in acetone (0.75 mL) and water (0.75 mL) was heated at 90° C. with stirring for 2 h. The reaction mixture was filtered through a short plug of diatomaceous earth (Celite®). The solvent was removed in vacuum, and the residue was partitioned between dichloromethane and water. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuum and the residue was purified by column chromatography on silica gel to give 2-chloro-8-phenyl-5,6,7,8-tetrahydroquinazoline (24.1 mg, 0.097 mmol, 52.4% yield) as white solid. LC-MS (M+H)+=245.1. 1H NMR (500 MHz, CDCl3) δ ppm 8.39 (1H, s), 7.27 (2H, t, J=7.6 Hz), 7.16-7.23 (1H, m), 6.95 (2H, d, J=7.3 Hz), 4.21 (1H, t, J=6.0 Hz), 2.72-2.91 (2H, m), 2.14-2.26 (1H, m), 1.95-2.06 (1H, m), 1.81-1.93 (1H, m), 1.71-1.81 (1H, m).

1. filtrationThe reaction mixture was filtered through a short plug of diatomaceous earth (Celite®)
2. customThe solvent was removed in vacuum
3. customthe residue was partitioned between dichloromethane and water
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with dichloromethane
6. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customThe solvent was removed in vacuum
9. customthe residue was purified by column chromatography on silica gel