Methanol → Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate

Participants

Reaction Steps

To a suspension of methanol 38 mL and acetic acid 38 mL of tert-butyl 2-nitro-4-phenylbenzoate 7.5 g was added iron powder 4.2 g at room temperature, and it was heated and refluxed for 1 hour. After the reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure. To the obtained residue, saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Hexane was added to the obtained residue, solid matter was filtrated to give tert-butyl 2-amino-4-phenylbenzoate 3.3 g of white solid.

Provenance & Evidence