反应详情

Oxalyl chloride (3.66 g, 0.0288 mol) was added dropwise to a stirred solution of 5-acetyl-2-ethoxybenzoic acid (3 g, 0.00144 mol) and dimethylformamide (0.1 ml) in dichloromethane (15 ml). The mixture was stirred at room temperature for 3 hours, then the solvent evaporated under vacuum and the residue azeotroped with hexane (3×50 ml). The crude acyl chloride was dissolved in dichloromethane (20 ml) and the solution added dropwise to a stirred solution of 2-amino-3-methylbenzamide (2.16 g, 0.0144 mol) in pyridine (40 ml) at 0° C. The mixture was allowed to warm to room temperature and stirred for a further 18 hours. The solvent was removed by evaporation under vacuum, the residue dissolved in dichloromethane (50 ml) and this solution then washed with saturated aqueous sodium carbonate solution (50 ml), 2N hydrochloric acid (50 ml) and brine (50 ml), then dried (Na2SO4) and evaporated under vacuum. Trituration of the residue with diethyl ether gave the title compound as a white solid (2.14 g, 44%), m.p. 214°-216° C. Found: C,66.81; H,5.98; N,8.16. C19H20N2O4 requires C,67.04; H,5.92; N,8.23%.

1. customthe solvent evaporated under vacuum
2. customthe residue azeotroped with hexane (3×50 ml)
3. dissolutionThe crude acyl chloride was dissolved in dichloromethane (20 ml)
4. temperatureto warm to room temperature
5. stirringstirred for a further 18 hours
6. customThe solvent was removed by evaporation under vacuum
7. dissolutionthe residue dissolved in dichloromethane (50 ml)
8. washthis solution then washed with saturated aqueous sodium carbonate solution (50 ml), 2N hydrochloric acid (50 ml) and brine (50 ml)
9. dry with materialdried (Na2SO4)
10. customevaporated under vacuum