7-Amino-3-chloro-3,4-dihydro-1H-quinolin-2-one synthesis

Yield:1116135-32-0 40%

Reaction Conditions:

with iron;acetic acid in water at 50; for 2 h;

Steps:

22.3

Iron powder (229 mmol) was added in several portions to a solution of methyl 2-chloro-3-(2,4- dinitrophenyl)propanoate (27.7 mmol) in acetic acid (75 mL) and water (5 mL) at 50 °C. The reaction mixture was maintained for 2 h at 50 °C and was allowed to cool to rt. The resulting solution was diluted with ethyl acetate (100 mL) and the precipitated solids were removed by filtration (5 x 200 mL ethyl acetate wash). The combined organic layers were washed with water (5 x 500 mL), dried (sodium sulfate), and concentrated to provide 7-amino-3-chloro-3,4-dihydroquinolin-2(lH)-one in 40% yield as a light yellow solid.

References:

WO2009/23844,2009,A2 Location in patent:Page/Page column 110-111