[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([NH:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:7]=1>[NH4+].[Cl-].C(O)C.[Fe]>[NH2:15][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[NH:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12]Iron powder (7 g, 0.12 mol) was added to a mixture of methyl 3-(5-bromo-2-nitrophenylamino)propanoate (12 g, 0.04 mol) in aq. NH4Cl solution (50 mL) and ethanol (100 mL). After heating at 60° C. for 2 h, the mixture solution was filtered. The filtrate was evaporated, diluted with water (100 mL), extracted with ethyl acetate (150 mL), dried and concentrated to give the crude product, which was purified by CombiFlash to afford methyl 3-((2-amino-5-bromophenyl)amino)propanoate (9.4 g, yield 84%). LRMS (M+H)+: 272 m/z. 1H NMR (300 MHz, CDCl3) δ 2.67-2.72 (d, 2H, J=6.3 Hz), 3.40-3.44 (d, 2H, J=6.3 Hz), 3.72 (s, 3H), 4.58 (br, 3H), 6.67-6.70 (d, 2H, J=8.1 Hz), 6.80-6.82 (m, 2H).
Loading…
