PAPER
Reduction of Carboxylic Acid Hydrazides to Amides
1467
precipitate was removed by filtration and washed with THF
(8) Bycroft, B. W.; Chan, W. C.; Chhabra, S. R.; Hone, N. D.
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(
10 mL) and EtOAc (10 mL). The combined organic filtrate was
concentrated to dryness and a biphenyl-contaminated crude product
was obtained (0.94 g). Purification by flash column chromatogra-
phy [silica gel, EtOAc–cyclohexane, 1:9 (removed excess biphe-
nyl), then 1:4 to 1:1] gave recovered 3 and product 2.
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3: Yield: 0.011 g (6%); R = 0.29 (EtOAc–cyclohexane, 2:3).
f
(
(
(
2
: Yield: 0.097 g (48%); R = 0.13 (EtOAc–cyclohexane, 2:3); yel-
f
lowish-white solid.
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Acknowledgment
This work was supported by the Deutsche Forschungsgemeinschaft
(Br2324/1-1), the Fonds der Chemischen Industrie, and the Univer-
106, 5594. (d) Gilchrist, T. L.; Hughes, D.; Wasson, R.
sity of Leipzig. We thank Jens Blechschmidt for very helpful syn-
thetic assistance, Prof. Bärbel Schulze for a donation of starting
materials, and Petra Gläser, Prof. B. Kersting, and Dr. V. Loszan for
providing the electroanalytical instruments and mercury. MJB
wishes to thank Dr. Howard D. Dewald for the dedicated introduc-
tion to electrochemistry.
Tetrahedron Lett. 1987, 28, 1573. (e) Meng, Q.; Hesse, M.
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Synthesis 2009, No. 9, 1463–1468 © Thieme Stuttgart · New York