反应详情

4-chlorobenzenamine 12.7 g (0.1 mol), and 470 mg BnEt3NCl was suspended in the mixture of 200 ml DCM, 200 ml CH3C1 and 200 ml 50% KOH (aq.), then was stirred at room temperature for 2 h. The organic phase was separated, washed with water (500 ml), dried with Na2SO4 and concentrated to afford yellow oil, which was purified by chromatography; 1-chloro-4-isocyanobenzene 500 mg, 2-hydroxynaphthalene-1,4-dione 635 mg (1.0 eq) and Paraformaldehyde 109 mg (1.0 eq) was dissolved in 30 ml toluene, stirred and refluxed under N2 for 4 h. After removing all solvents under reduced pressure, the residue was purified by chromatography to afford 2-(4-chlorophenylamino)naphtho[2,3-b]furan-4,9-dione as black solid. 1H NMR (300 MHz, DMSO) δ6.39 (s, 1H); 7.24˜7.29 (m, 2H); 7.41˜7.43 (dd, 2H); 7.54 (br, 1H); 7.69˜7.73 (t, 1H); 7.78˜7.82 (t, 1H); 8.13˜8.17 (t, 3H) ppm. MS-ESI: cal. 323; found: 346 (M+Na).

1. customThe organic phase was separated
2. washwashed with water (500 ml)
3. dry with materialdried with Na2SO4
4. concentrationconcentrated
5. customto afford yellow oil, which
6. customwas purified by chromatography
7. stirringstirred
8. temperaturerefluxed under N2 for 4 h
9. customAfter removing all solvents under reduced pressure
10. customthe residue was purified by chromatography