反应详情

N-(Mesityl)-oxanilic acid ethyl ester (5.23 g, 24.4 mmol, 1 eq) and 2-aminophenol (2.67 g, 24.4 mmol, 1.0 eq) were dissolved in toluene (50 ml), forming a suspension. To this suspension was added triethylamine (6.8 ml, 50 mmol, 2 eq). The suspension was then heated to reflux, causing the solids to dissolve. After heating at reflux overnight, the product precipitated. At this point, ethyl acetate was added until the precipitate redissolved. The solution was then washed with 2 M HCl solution (2×100 ml). The aqueous layer was then washed with ethyl acetate, and the combined organic layers were washed with brine (100 ml), and dried over MgSO4. The solvent was then removed under reduced pressure, leaving a yellowish solid. The yellowish solid was then recrystallized from toluene, producing a product, white crystalline solid (5.26 g, 17.7 mmol, 72.4% yield). 1H NMR (300 MHz, CDCl3) δ 9.69 (s, 1H), 8.84 (s, 1H), 8.11 (s, J=7.7 Hz, 1H), 7.51 (dd, J=8.0, 1.8 Hz, 1H), 7.14 (ddd, J=1.5, 8.1, 7.2 Hz, 1H), 6.92 (m, 3H), 2.30 (s, 3H), 2.22 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 158.2, 157.9, 148.2, 138.2, 134.9, 129.5, 129.4, 127.7, 124.3, 122.2, 121.1, 118.9, 21.2, 18.6. Anal. Calcd for C17H18N2O3: C, 68.44; H, 6.08; N, 9.39. Found: C, 68.50; H, 5.96; N, 9.44.

1. customforming a suspension
2. temperatureThe suspension was then heated
3. temperatureto reflux
4. dissolutionto dissolve
5. temperatureAfter heating
6. temperatureat reflux overnight
7. customthe product precipitated
8. additionAt this point, ethyl acetate was added until the precipitate
9. dissolutionredissolved
10. washThe solution was then washed with 2 M HCl solution (2×100 ml)
11. washThe aqueous layer was then washed with ethyl acetate
12. washthe combined organic layers were washed with brine (100 ml)
13. dry with materialdried over MgSO4
14. customThe solvent was then removed under reduced pressure
15. customleaving a yellowish solid
16. customThe yellowish solid was then recrystallized from toluene