methyl 3-(2-amino-N-benzylanilino)-3-oxopropanoate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: methyl 3-((2-aminophenyl)(benzyl)amino)-3-oxopropanoate (200 mg, 0.67 mmol) was dissolved in 10 mL of EtOH and cooled to 0° C., and Na metal (25 mg, 1.07 mmol) was added. The reaction mixture was warmed to room temperature and stirred for 1 h. The mixture was concentrated and the residue was purified by prep-TLC to give 1-benzyl-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione (160 mg, 89%). 1H NMR (300 MHz, DMSO): δ 2.89 (d, J=9.9 Hz, 1H), 3.03 (d, J=10.2 Hz, 1H), 3.46 (q, J=21 Hz, 2H), 6.68 (t, J=8.1 Hz, 1H), 6.84-6.91 (m, 2H), 7.08-7.28 (m, 6H). The reaction mixture was warmed to room temperature The mixture was concentrated the residue was purified by prep-TLC

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron powder (3 g) was added to a solution of methyl 3-(benzyl(2-nitrophenyl)amino)-3-oxopropanoate (400 mg, 1.22 mmol) in EtOH (10 mL) and NH4Cl (10 mL). The reaction mixture was heated at 70° C. for 2 h. The mixture was filtered off and the filtrate was extracted by EA (50 mL), the separated organic layer was dried over Na2SO4. After the solvent was removed in vacuum, the residue was purified by combi-flash to give methyl 3-((2-aminophenyl)(benzyl)amino)-3-oxopropanoate as a yellow solid (200 mg, 55%). LRMS (M+H)+: 298 m/z. The mixture was filtered off the filtrate was extracted by EA (50 mL) the separated organic layer was dried over Na2SO4 After the solvent was removed in vacuum the residue was purified by combi-flash