methyl 3-(2-aminoanilino)propanoate

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

Procedure: Sodium (1.8 g, 77.2 mmol) was added in portions to methanol (50 mL), and the mixture was stirred for 1 h. The resulting mixture was added dropwise to a solution of methyl 3-((2-aminophenyl)amino)propanoate (9.4 g, 48.2 mmol) in methanol (150 mL) at 0° C. Once addition was completed, the mixture was stirred at room temperature overnight. The mixture was concentrated, and the residue was purified by CombiFlash (PE:EA=5:1) to give 4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one as a yellow solid (3.9 g, 50%). LRMS (M+H)+: 161 m/z. 1H NMR (300 MHz, CD3OD): δ 2.61 (t, J=6.0 Hz, 2H), 3.62 (t, J=6.0 Hz, 2H), 6.76-6.86 (m, 2H), 6.90-6.99 (m, 2H). Once addition the mixture was stirred at room temperature overnight The mixture was concentrated the residue was purified by CombiFlash (PE:EA=5:1)

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

Procedure: A mixture of methyl 3-((2-nitrophenyl)amino)propanoate (11 g, 48.9 mmol) and Pd/C (3.3 g, 10%) in 300 mL of MeOH and 20 mL of EtOAc was stirred overnight under H2 atmosphere at room temperature. The mixture was filtered off, and the filtrate was concentrated to give methyl 3-((2-aminophenyl)amino)propanoate as a yellow oil. (9.3 g, 98%). LRMS (M+H)+: 193 m/z. The mixture was filtered off the filtrate was concentrated