反应详情

温度

60 °C

To a solution of 2-(4-aminobenzyl)-5,6-bis(4-methoxyphenyl)-2H-pyridazin-3-one (245 mg, 0.6 mmol) in acetone/N,N-dimethylformamide (5/1) (6 ml), sodium hydrogencarbonate (378 mg, 4.5 mmol) and a solution of dimethyl sulfate in acetone [an acetone solution of dimethyl sulfate (631 mg) (total volume: 5 ml); 3.0 ml, 3.0 mmol)] was added, followed by stirring under heat at 60° C. for 90 minutes. After the acetone was distilled off, the residue was extracted with ethyl acetate. The organic layer was washed successively with water and a brine, and was then dried over anhydrous sodium sulfate. The solvent was distilled off. The pale orange oil (238 mg) was separated and purified by silica gel preparative chromatography [developer: chloroform/methanol (20/1)], whereby 5,6-bis(4-methoxyphenyl)-2-[4-(dimethylamino)benzyl]-2H-pyridazin-3-one (80.6 mg, 30.8%) was obtained as a reddish brown oil from fractions having large Rf values. 1H-NMR (CDCl3) δ: 2.94(6H,s), 3.79(6H,s), 5.32(2H,s), 6.71(2H,d,J=8.79 Hz), 6.78(2H,d,J=8.79 Hz), 6.79(2H,d,J=9.03 Hz), 6.85(1H,s), 7.07(2H,d,J=8.79 Hz), 7.11(2H,d,J=9.03 Hz), 7.48(2H,d,J=8.79 Hz).

1. addition3.0 ml, 3.0 mmol)] was added
2. distillationAfter the acetone was distilled off
3. extractionthe residue was extracted with ethyl acetate
4. washThe organic layer was washed successively with water
5. dry with materiala brine, and was then dried over anhydrous sodium sulfate
6. distillationThe solvent was distilled off
7. customThe pale orange oil (238 mg) was separated
8. custompurified by silica gel preparative chromatography [developer: chloroform/methanol (20/1)]