ethyl 6-amino-1-benzofuran-3-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of ethyl 6-amino-1-benzofuran-3-carboxylate (2.0 g, 9.8 mmol) in 50 mL of MeOH was added Mg filings (1.17 g, 49 mmol) ans the mixtrue was stired overnight at room temperature. The mixture was filtered and the filtrate was concentrated. The residue was then partitioned between EtOAc and water. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified with silca gel column chromatograph to give methyl 6-amino-2,3-dihydro-1-benzofuran-3-carboxylate. was added Mg filings (1.17 g, 49 mmol) The mixture was filtered the filtrate was concentrated The residue was then partitioned between EtOAc and water The combined organic phase was washed with brine dried over anhydrous sodium sulfate concentrated The residue was purified with silca gel column chromatograph

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of ethyl 6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-benzofuran-3-carboxylate (4.7 g, 14.0 mmol) in 200 mL of EtOH was added NH2NH2H2O (6.3 mL, 107.1 mmol, 85% in water) dropwise and the mixture was stired for 2 h at room temperature. The solvent was removed under vacuum and the residue was dissolved in water. The mixture was extracted with EtOAc, and the combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified with silca gel column chromatograph to give ethyl 6-amino-1-benzofuran-3-carboxylate. The solvent was removed under vacuum the residue was dissolved in water The mixture was extracted with EtOAc the combined organic phase was washed with brine dried over anhydrous sodium sulfate concentrated The residue was purified with silca gel column chromatograph