反应详情

温度

80 °C

To a mechanically stirred suspension of N-(2-cyano-5-methylphenyl)-2-methoxybenzamide (180 g, 0.67 mol) in 1.8 L ethanol under an N2 atmosphere was added 6 N sodium hydroxide solution (310 g in 1.25 L water). To the above mixture, 30% hydrogen peroxide (350 mL, 3.64 mol) was slowly added. The solution was then slowly heated to 80° C. and maintained at this temperature for 4 h. The reaction mixture was concentrated under reduced pressure to remove ethanol, giving a suspension which was quenched with ice cold water (1.8 L) and acidified with acetic acid to pH 5-6 to give a solid residue. The solid was filtered and washed with water, then dissolved in 5.5 L CH2Cl2 and washed with water (2×18 L). The organic layer was dried over sodium sulfate, and the solvent was removed under reduced pressure to give a light yellow solid (100 g, 54%). mp 165-170° C. 1H NMR (CDCl3) δ 2.429 (s, 3H), 4.2 (s, 3), 6.8-7.2 (m, 3H), 7.4-7.6 (m, 2H), 8.2-8.4 (d, 1H), 8.6 (s, 1H), 10.8 (bs, 1H) ppm; 13CNMR (CDCl3) δ21.68, 55.6, 111.3, 118.2, 119.6, 121.1, 125.7, 127.14, 127.64, 130.96, 132.56, 144.9, 149.06, 150.42, 157.25, 161.52. M/z (obs., [m+H]+)=268.

1. temperaturemaintained at this temperature for 4 h
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. customto remove ethanol
4. customgiving a suspension which
5. customwas quenched with ice cold water (1.8 L)
6. customto give a solid residue
7. filtrationThe solid was filtered
8. washwashed with water
9. dissolutiondissolved in 5.5 L CH2Cl2
10. washwashed with water (2×18 L)
11. dry with materialThe organic layer was dried over sodium sulfate
12. customthe solvent was removed under reduced pressure