反应详情

In one portion of 4.00 g (0.013 mole) of 3-amino-1-(4-fluorophenyl)-2,3-dihydro-5-methoxy-1H-indol-2-one hydrochloride in 80 ml of anhydrous dichloroethane, 2.69 g (0.0182 mole, 1.4 equivalent) of phthalic anhydride was added to a stirred suspension under argon atmosphere. 2 ml (0.0143 mole) of triethylamine was added dropwise to this mixture over 10 minutes. Then, after the whole was stirred at room temperature for 10 minutes, it was further refluxed over an oil bath overnight. Excessive phthalic anhydride was decomposed by adding a mixture of 2 ml of triethylamine and 2 ml of methanol and refluxing the resulting mixture for 20 minutes. The reaction mixture was concentrated under reduced pressure and then extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried. The residue obtained by removing ethyl acetate by evaporation was recrystallized from hexane-ethyl acetate to afford 4.50 g of 3-(1,2-dihydro-1,3-dioxoisoindol-2-yl)-1-(4-fluorophenyl)-2,3-dihydro-5-methoxy-1H-indol-2-one as colorless crystals. Melting point: 208.5° to 210.0° C., IR (Nujol) (cm-1): 1730, 1715, 1495, 1400, 1225, 1210, 750, 715, MS (DI, m/e): 402 (M+, base), 227, 184, 76.

1. temperatureit was further refluxed over an oil bath overnight
2. additionby adding
3. temperaturerefluxing the resulting mixture for 20 minutes
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. extractionextracted with ethyl acetate
6. washThe ethyl acetate layer was washed with water
7. customdried
8. customThe residue obtained
9. customby removing ethyl acetate
10. customby evaporation
11. customwas recrystallized from hexane-ethyl acetate