1-(3-Chlorophenyl)ethanone → 1-(5-Chloro-2-nitrophenyl)ethanone

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The intermediates, 5-alkylamino-2-aminoacetophenones (60-62) were prepared according to the methods reported before. As shown in Scheme 6, the starting 3-chloroacetophenone (54) was first nitrated with HNO3/H2SO4 to form the 5-chloro-2-nitroacetophenone (55) and 5-chloro-4-nitroacetophenone (56). Compound 55 was reacted separately with various alkylamines to yield the corresponding 5-alkylamino-2-nitroacetophenones (57-59). Catalytic hydrogenation of compounds 57-59 yielded the corresponding 5-alkylamino-2-aminoacetophenones (60-62). L. Ll, K. K. Wang, S. C. Kuo, T. S. Wu, D. Lednicer, C. M. Lin, E. Hamel and K. H. Lee, J. Med. Chem., 37, 1126-35. (1994), which is herein incorporated by reference in its entirety.

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