反应详情

温度

130 °C

To a 6.82 g (17.5 mmol) sample of the beta-ketoester from step 3 was added 3.89 g (26.1 mmol) of triethyl orthoformate and 8.00 g (78 mmol) of acetic anhydride, and the reaction was stirred at 130° C. for 2.5 hours. The volatile materials were then removed under reduced pressure, and toluene was added and distilled from the residue to remove any remaining reagents. The dried residue was then dissolved in 150 mL of methylene chloride and 1.91 g (17.5 mmol) of o-aminophenol was added. The reaction was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the residue was washed with ether, filtered and dried to afford 7.59 g of the title compound as a yellow solid, mp 221° C. (dec). MS M/Z: 510 (M+H). IR (KBr): 1623, 1643, 1684 cm-1. NMR (DMSO) d: 1.10 (m, 3H), 1.82 (m, 3H), 2.05 (m, 2H), 3.64 (m, 2H), 3.80 (m, 4H), 4.04 (m, 2H), 6.95 (m, 1H), 7.10 (m, 1H), 7.58 (m, 1H), 8.16 (m, 1H), 8.65 (m, 1H), 10.60 (m, 1H), 12.73 (m, 1 H). Analysis calculated for C24H23F4N3O5 : C, 56.58; H, 4.55; N, 8.25. Found: C, 56.30; H, 4.63; N, 8.22.

1. customThe volatile materials were then removed under reduced pressure, and toluene
2. additionwas added
3. distillationdistilled from the residue
4. customto remove any remaining reagents
5. dissolutionThe dried residue was then dissolved in 150 mL of methylene chloride
6. stirringThe reaction was stirred at room temperature overnight
7. customThe solvent was removed under reduced pressure
8. washthe residue was washed with ether
9. filtrationfiltered
10. customdried