反应详情

Iron powder (2.5 g, 44.7 mmol) was added portion wise to a solution of ethyl 2-(2-chloro-5-nitrophenyl)acetate (8 g, 4.68 mmol) and cone. HCl (12 M, 3.9 mL, 46.8 mmol) in EtOH (100 mL). The resultant mixture was heated at 50° C. for 2 hour. The mixture was filtered and the filtrate cake was washed with saturated aqueous Na2CO3 until pH 8. The filter cake was further washed with EtOAc and the combined filtrates were partitioned between EtOAc and water. The organics were dried over Na2SO4 and concentrated in vacuo to provide ethyl 2-(5-amino-2-chlorophenyl)acetate (5.6 g, 56% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.00 (d, J=8.4 Hz, 1 H), 6.50 (s, J=2.8 Hz, 1 H), 6.44 (dd, J=8.4 Hz, 2.8 Hz, 1H), 5.20 (s, 2 H), 4.05 (q, J=7.2 Hz, 2 H), 3.56 (s, 2 H), 1.15 (t, J=7.2 Hz, 3 H).

1. filtrationThe mixture was filtered
2. washthe filtrate cake was washed with saturated aqueous Na2CO3 until pH 8
3. washThe filter cake was further washed with EtOAc
4. customthe combined filtrates were partitioned between EtOAc and water
5. dry with materialThe organics were dried over Na2SO4
6. concentrationconcentrated in vacuo