反应详情

温度

0 °C

A mixture of 2 g of (2-methoxy-4-methylphenyl)methanamine (from step 3) and Et3N (3.7 mL, 2 eq) in dry CH3CN (45 mL) was cooled to 0° C. under N2 atmosphere and ethyl 2-chloro-2-oxoacetate (1.47 mL, 1 eq) was added dropwise. After the addition was complete, the reaction mixture was stirred at room temperature for 4 hours and 2-(5-methylpyridin-2-yl)ethanamine (2.52 g, 1.4 eq, from step 5) was added. The reaction was heated at reflux for 24 hours. After cooling the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (eluent: 25-35% acetone in hexane) and recrystallized from ethyl acetate/hexane and ethanol/water to give 650 mg of N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl)oxalamide (15%).

1. additionAfter the addition
2. temperatureThe reaction was heated
3. temperatureat reflux for 24 hours
4. temperatureAfter cooling the solvent
5. customwas removed under reduced pressure
6. dissolutionthe residue was dissolved in ethyl acetate
7. washwashed successively with water and brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customevaporated
11. customThe residue was chromatographed on silica gel (eluent: 25-35% acetone in hexane)
12. customrecrystallized from ethyl acetate/hexane and ethanol/water