反应详情

N-(3-amino-6-methoxyphenyl)acetamide 25 (1.0 gm, 0.0055 moles) was dissolved in 30 ml DCM at room temperature under argon with stirring. Diisopropylethylamine (4.83 ml, 0.028 moles) and dimethylsulfate (2.36 ml, 0.025 moles) were added. After stirring at room temperature for 8 hours, 30 ml DCM and 40 ml 0.3 N NaOH were added. The mixture was partitioned and the aqueous layer was washed with three 30 ml portions of DCM. The combined organic extract was washed with saturated NaCl, dried over MgSO4, filtered, and concentrated to give N-(3-dimethylamino-6-methoxyphenyl)acetamide 26 (0.57 gm, 50%). 1H NMR (CDCl3) δ 8.01, 1H, m; 7.75, 1H, br s; 6.79, 1H, d; 6.43, 1H, dd; 3.82, 3H, s; 2.89, 6H, s, 2.19; 3H, s.

1. stirringAfter stirring at room temperature for 8 hours
2. customThe mixture was partitioned
3. washthe aqueous layer was washed with three 30 ml portions of DCM
4. extractionThe combined organic extract
5. washwas washed with saturated NaCl
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated