反应详情

温度

0 °C

A mixture of Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one (120.0 mg, 0.571 mmol), paraformaldehyde (17.1 mg, 0.571 mmol), and butylamine (56.4 μL, 0.571 mmol) in 5.5 mL of EtOH was heated at reflux for 2.5 h. Then reaction mixture was treated with 2 mL of hexane was and then cooled to 0° C. The reaction mixture was then filtered to remove Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one. The filtrate was partitioned between dilute HCl and ethyl acetate. The organic layer was removed and the aqueous layer washed with 15 mL Ethyl acetate. The aqueous phase was made basic to pH 8 with saturated NaHCO3 and extracted with ethyl acetate. The ethyl acetate layer was washed with H2O, brine and dried over anhydrous Na2SO4. The solvent was removed in vacuo to give 58 mg of yellow oil. The oil was purified by chromatography (silica gel, 1:1/hexane:ethyl acetate) to give the title compound (51.6 mg, 31%) as a yellow solid.

1. temperaturewas heated
2. temperatureat reflux for 2.5 h
3. customThen reaction mixture
4. filtrationThe reaction mixture was then filtered
5. customto remove Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one
6. customThe filtrate was partitioned between dilute HCl and ethyl acetate
7. customThe organic layer was removed
8. washthe aqueous layer washed with 15 mL Ethyl acetate
9. extractionextracted with ethyl acetate
10. washThe ethyl acetate layer was washed with H2O, brine
11. dry with materialdried over anhydrous Na2SO4
12. customThe solvent was removed in vacuo