Benzoyl chloride → N-hydroxy-7-(naphthalen-2-yl)-7-oxoheptanamide

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Reaction Steps

Following the procedure described in Example 18, step 1, 2, 3, but substituting respectively ethyl-6-iodohexanoate for ethyl-7-iodoheptanoate and 2-naphthoyl chloride for benzoyl chloride, and then the resulting carboxylic acid was substituted for 37 in Example 14, step 3, using 1.1 equivalent of NH2OH.HCl and triethylamine each, to afford the title compound 111 in 55% yield. 1H NMR (300 MHz, 20% CD3OD in CDCl3): δ 8.47 (s, 1H), 8.05-7.50 (m, 6H), 3.12 (br t, 2H), 2.15 (br t, 2H), 1.82-1.60 (m, 4H), 1.46 (m, 2H). 13C NMR (75 MHz, 20% CD30D in CDCl3): δ 23.59, 25.02, 28.36, 32.33, 38.06, 123.40, 126.56, 127.46, 128.21, 128.29, 129.29, 129.60, 132.25, 133.78, 135.37, 171.04, 201.04.

Provenance & Evidence