ethyl 3-(2-aminoanilino)butanoate

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

Procedure: An round bottomed flask was charged with ethyl 3-(2-aminophenylamino)butanoate (684 mg, 3.08 mmol) and a stirbar. MeOH (15 mL, 0.1 M) was added, followed by sodium methoxide (249 mg, 4.62 mmol), and the solution was stirred at reflux for 48 h. The mixture was concentrated with celite and purified by silica gel chromatography (eluting with hexanes/ethyl acetate) to yield 4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one as an off-white amorphous solid (0.22 g, 1.25 mmol, 41%). at reflux for 48 h The mixture was concentrated with celite purified by silica gel chromatography (eluting with hexanes/ethyl acetate)

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

Procedure: A round bottomed flask was charged with palladium on carbon (327 mg, 0.308 mmol) and a stirbar. Ethyl 3-(2-nitrophenylamino)butanoate (776 mg, 3.08 mmol) in 1:1 EtOH:EtOAc (40 mL) was added, and the flask was evacuated and purged with hydrogen three times. Stirred at room temperature for 3 h. The mixture was filtered and concentrated to yield ethyl 3-(2-aminophenylamino)butanoate as an oil. the flask was evacuated purged with hydrogen three times The mixture was filtered concentrated