反应详情

To a solution of N-methyl-N-(4-picolyl)amine (0.40 g, 3.3 mmol) and triethylamine (1.5 mL, 10.8 mmol) in CH2Cl2 (15 mL) was added 4-methoxybenzoyl chloride (1.2 g, 7.3 mmol). The resulting mixture was stirred at rt for 15 min, and then partitioned between 2.5N NaOH and Et2O. The organic extract was washed with saturated aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with a solvent gradient of 2-4% MeOH/CHCl3. The material that was isolated was triturated with Et2O to provide the title compound as a light yellow solid (0.18 g, 21%): 1H NMR (CDCl3): d 8.60 (d, 2H); 7.43 (br d, 2H); 7.20 (br s, 2H); 6.90 (br d, 2H); 4.66 (br s, 2H); 3.80 (s, 3H); 3.00 (s, 3H).

1. custompartitioned between 2.5N NaOH and Et2O
2. extractionThe organic extract
3. washwas washed with saturated aqueous NaCl
4. dry with materialdried (MgSO4)
5. customThe solvent was removed in vacuo
6. customthe residue was purified by flash chromatography
7. washeluting with a solvent gradient of 2-4% MeOH/CHCl3
8. customThe material that was isolated
9. customwas triturated with Et2O