[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([NH:10]C(=O)C)=[C:4]([CH3:14])[CH:3]=1.Cl.[OH-].[Na+]>CO>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([NH2:10])=[C:4]([CH3:14])[CH:3]=1N-(4-bromo-5-methoxy-2-methylphenyl)acetamide was dissolved in methanol (15 mL) and concentrated HCl (30 mL). The mixture was refluxed at 95° C. overnight. After cooling to room temperature, the mixture was poured into ice water, and basified to pH=12 with conc. NaOH aqueous solution. The mixture was then extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over Na2SO4 and concentrated. The crude product was purified by silica chromatography (15% ethyl acetate in hexanes) to give 4-bromo-5-methoxy-2-methylaniline as a beige solid; 1H NMR (400 mHz, CDCl3) 7.20 (s, 1H), 6.37 (s, 1H), 4.6 (br, 2H), 3.82 (s, 3H), 2.12 (s, 3H).
Wird geladen…
