反应详情

温度

20 °C

o-(Bromoacetyl)phenyl acetate (2.57 g, 10 mmol) in dry acetone (30 mL) was treated with thionicotinamide (1.38 g, 10 mmol). The mixture was refluxed 16 hours, cooled to about 20° C. at which point a precipitate formed (2.46 g). The precipitate was filtered and dried in vacuo. The precipitate was dissolved in MeOH (50 mL) and treated with 10% NaOH in H2O (20 mL) for 1 hour at about 20° C. to hydrolyze the acetate ester. The pH was adjusted to neutrality with 6N HCl while chilling on ice/H2O and the volume was reduced to about 35 mL in vacuo. After cooling to about 4° C., an orange solid precipitate formed, which was removed by filtration and dried in vacuo to constant mass to yield 36-50% product (LSIMS m/s 254 (MH+)).

1. temperatureThe mixture was refluxed 16 hours
2. customformed (2.46 g)
3. filtrationThe precipitate was filtered
4. customdried in vacuo
5. dissolutionThe precipitate was dissolved in MeOH (50 mL)
6. additiontreated with 10% NaOH in H2O (20 mL) for 1 hour at about 20° C.
7. temperaturewhile chilling on ice/H2O
8. temperatureAfter cooling to about 4° C.
9. customan orange solid precipitate formed
10. customwhich was removed by filtration
11. customdried in vacuo to constant mass