Water → 7H-1,3-Benzodioxolo[4,5-f]isoindole-7,9(8H)-dione, 10-(1,3-benzodioxol-5-yl)-8-(3-hydroxypropyl)-

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Reaction Steps

3-Amino-1-propanol (27 mg, 0.36 mmol) in toluene (5 mL) at 0° C. was added dropwise to a stirred solution of anhydride 1 (109 mg, 0.3 mmol) in toluene (40 mL). The mixture was stirred at room temperature for 1 h and then heated under Dean-Stark trap for 3 h. After water ceased to distill, the reaction mixture was cooled, washed successively with water (2×50 mL), 5% aqueous NaHCO3 solution (2×50 mL), and water (2×50 mL), and then dried over MgSO4. The solvent was removed in vacuo, and the resulting product was purified by column chromatography on silica gel using CH2Cl2/acetone (3:1 to 1:1, v/v) to provide 29 (10 mg, 11%) as a pale yellow powder. mp 150-152° C.; 1H NMR (CDCl3) δ 8.27 (s, 1H, H4), 7.56 (d, 1H, H5, J=8.4 Hz), 7.26 (d, 1H, H6, J=8.4 Hz), 6.86-6.91 (m, 3H, H2′+H5′+H6′), 6.04 (s, 2H, 3′,4′-OCH2O—), 5.97 (s, 2H, 7,8-OCH2O—), 3.69-3.76 (m, 4H, NCH2CH2CH2OH), 1.83 (m, 2H, NCH2CH2CH2OH).

Provenance & Evidence