Sodium → 2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

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Reaction Steps

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).

Provenance & Evidence